| 2009-04-06 | vs NYA | 1 | W 10-5 | 0-1 | 2 | 48,607 | Jeremy Guthrie | CC Sabathia | Jeremy Guthrie | CC Sabathia | | 10 | 5 | 5 |
| 2009-04-08 | vs NYA | 2 | W 7-5 | 1-1 | 1 | 22,856 | Koji Uehara | Chien-Ming Wang | Koji Uehara | Chien-Ming Wang | George Sherrill | 17 | 10 | 7 |
| 2009-04-09 | vs NYA | 3 | L 2-11 | 2-1 | 1 | 28,534 | Alfredo Simon | A.J. Burnett | A.J. Burnett | Alfredo Simon | | 19 | 21 | -2 |
| 2009-04-10 | vs TBA | 4 | W 5-4 | 3-1 | 1 | 22,866 | Mark Hendrickson | Andy Sonnanstine | Mark Hendrickson | Andy Sonnanstine | George Sherrill | 24 | 25 | -1 |
| 2009-04-11 | vs TBA | 5 | W 6-0 | 4-1 | 1 | 15,108 | Jeremy Guthrie | Jeff Niemann | Jeremy Guthrie | Jeff Niemann | | 30 | 25 | 5 |
| 2009-04-12 | vs TBA | 6 | L 3-11 | 5-1 | 1 | 15,531 | Adam Eaton | James Shields | James Shields | Adam Eaton | | 33 | 36 | -3 |
| 2009-04-13 | @ TEX | 7 | W 10-9 | 5-2 | 1 | 12,184 | Koji Uehara | Vicente Padilla | Koji Uehara | Vicente Padilla | George Sherrill | 43 | 45 | -2 |
| 2009-04-14 | @ TEX | 8 | W 7-5 | 6-2 | 1 | 14,041 | Alfredo Simon | Brandon McCarthy | Jim Johnson | Eddie Guardado | | 50 | 50 | 0 |
| 2009-04-15 | @ TEX | 9 | L 6-19 | 7-2 | 1 | 17,539 | Mark Hendrickson | Kris Benson | Kris Benson | Mark Hendrickson | | 56 | 69 | -13 |
| 2009-04-17 | @ BOS | 10 | L 8-10 | 8-2 | 1 | 38,266 | Jeremy Guthrie | Brad Penny | Ramon Ramirez | Danys Baez | Jonathan Papelbon | 64 | 79 | -15 |
| 2009-04-18 | @ BOS | 11 | L 4-6 | 8-3 | 2 | 37,559 | Adam Eaton | Josh Beckett | Josh Beckett | Adam Eaton | Jonathan Papelbon | 68 | 85 | -17 |
| 2009-04-19 | @ BOS | 12 | L 1-2 | 8-4 | 2 | 37,869 | Koji Uehara | Jon Lester | Jon Lester | Koji Uehara | Takashi Saito | 69 | 87 | -18 |
| 2009-04-20 | @ BOS | 13 | L 1-12 | 8-5 | 2 | 37,865 | Mark Hendrickson | Justin Masterson | Justin Masterson | Mark Hendrickson | | 70 | 99 | -29 |
| 2009-04-21 | vs CHA | 14 | W 10-3 | 8-6 | 2 | 14,801 | Brad Bergesen | Jose Contreras | Brad Bergesen | Jose Contreras | | 80 | 102 | -22 |
| 2009-04-22 | vs CHA | 15 | L 2-8 | 8-7 | 2 | 10,868 | Jeremy Guthrie | John Danks | John Danks | Jeremy Guthrie | | 82 | 110 | -28 |
| 2009-04-23 | vs CHA | 16 | W 6-2 | 9-7 | 2 | 11,723 | Adam Eaton | Bartolo Colon | Adam Eaton | Bartolo Colon | | 88 | 112 | -24 |
| 2009-04-24 | vs TEX | 17 | L 4-5 | 9-8 | 4 | 24,319 | Koji Uehara | Vicente Padilla | C.J. Wilson | George Sherrill | Frank Francisco | 92 | 117 | -25 |
| 2009-04-25 | vs TEX | 18 | L 5-6 | 9-9 | 4 | 41,160 | Mark Hendrickson | Scott Feldman | Scott Feldman | Mark Hendrickson | Frank Francisco | 97 | 123 | -26 |
| 2009-04-26 | vs TEX | 19 | W 8-5 | 10-9 | 4 | 22,896 | Brad Bergesen | Brandon McCarthy | Danys Baez | Jason Jennings | George Sherrill | 105 | 128 | -23 |
| 2009-04-27 | vs TEX | 20 | L 4-6 | 10-10 | 4 | 10,621 | Jeremy Guthrie | Matt Harrison | Matt Harrison | Matt Albers | Frank Francisco | 109 | 134 | -25 |
| 2009-04-28 | vs ANA | 21 | L 5-7 | 10-11 | 4 | 11,857 | Adam Eaton | Joe Saunders | Joe Saunders | Adam Eaton | Brian Fuentes | 114 | 141 | -27 |
| 2009-04-29 | vs ANA | 22 | L 2-3 | 10-12 | 4 | 14,203 | Koji Uehara | Shane Loux | Shane Loux | Koji Uehara | Brian Fuentes | 116 | 144 | -28 |
| 2009-05-01 | @ TOR | 23 | L 4-8 | 10-13 | 4 | 20,202 | Mark Hendrickson | Roy Halladay | Roy Halladay | Mark Hendrickson | | 120 | 152 | -32 |
| 2009-05-02 | @ TOR | 24 | L 4-5 | 10-14 | 4 | 18,331 | Brad Bergesen | Robert Ray | Jason Frasor | Brian Bass | | 124 | 157 | -33 |
| 2009-05-03 | @ TOR | 25 | L 3-4 | 10-15 | 5 | 20,418 | Jeremy Guthrie | Scott Richmond | Scott Richmond | Jeremy Guthrie | Scott Downs | 127 | 161 | -34 |
| 2009-05-04 | @ TBA | 26 | W 8-4 | 11-15 | 4 | 12,658 | Adam Eaton | Scott Kazmir | Danys Baez | Scott Kazmir | | 135 | 165 | -30 |
| 2009-05-05 | @ TBA | 27 | L 3-6 | 11-16 | 5 | 13,174 | Koji Uehara | Matt Garza | Matt Garza | Koji Uehara | Troy Percival | 138 | 171 | -33 |
| 2009-05-06 | vs MIN | 28 | W 4-1 | 12-16 | 5 | 10,566 | Mark Hendrickson | Kevin Slowey | Brian Bass | Kevin Slowey | | 142 | 172 | -30 |
| 2009-05-07 | vs MIN | 29 | W 5-4 | 13-16 | 5 | 11,399 | Brad Bergesen | Glen Perkins | Jim Johnson | Jose Mijares | George Sherrill | 147 | 176 | -29 |
| 2009-05-08 | vs NYA | 30 | L 0-4 | 13-17 | 5 | 36,926 | Jeremy Guthrie | CC Sabathia | CC Sabathia | Jeremy Guthrie | | 147 | 180 | -33 |
| 2009-05-09 | vs NYA | 31 | W 12-5 | 13-18 | 5 | 41,825 | Adam Eaton | Phil Hughes | Adam Eaton | Phil Hughes | | 159 | 185 | -26 |
| 2009-05-10 | vs NYA | 32 | L 3-5 | 13-19 | 5 | 33,290 | Koji Uehara | Joba Chamberlain | Joba Chamberlain | Jim Johnson | Mariano Rivera | 162 | 190 | -28 |
| 2009-05-12 | vs TBA | 33 | W 7-5 | 14-19 | 4 | 17,122 | Mark Hendrickson | Andy Sonnanstine | Brian Bass | Andy Sonnanstine | George Sherrill | 169 | 195 | -26 |
| 2009-05-13 | vs TBA | 34 | L 6-8 | 14-20 | 5 | 13,237 | Brad Bergesen | Jeff Niemann | Jeff Niemann | Brad Bergesen | J.P. Howell | 175 | 203 | -28 |
| 2009-05-14 | @ KCA | 35 | W 9-5 | 15-20 | 5 | 24,431 | Jeremy Guthrie | Gil Meche | Jeremy Guthrie | Gil Meche | | 184 | 208 | -24 |
| 2009-05-15 | @ KCA | 36 | L 1-8 | 15-21 | 5 | 38,353 | Adam Eaton | Zack Greinke | Zack Greinke | Adam Eaton | | 185 | 216 | -31 |
| 2009-05-16 | @ KCA | 37 | W 3-2 | 16-21 | 5 | 26,720 | Rich Hill | Kyle Davies | Rich Hill | Kyle Davies | George Sherrill | 188 | 218 | -30 |
| 2009-05-17 | @ KCA | 38 | L 4-7 | 16-22 | 5 | 22,791 | Koji Uehara | Luke Hochevar | Juan Cruz | Jim Johnson | | 192 | 225 | -33 |
| 2009-05-19 | @ NYA | 39 | L 1-9 | 16-23 | 5 | 42,838 | Brad Bergesen | CC Sabathia | CC Sabathia | Brad Bergesen | | 193 | 234 | -41 |
| 2009-05-20 | @ NYA | 40 | L 4-11 | 17-23 | 5 | 43,903 | Jeremy Guthrie | Phil Hughes | Phil Hughes | Jeremy Guthrie | Mariano Rivera | 197 | 245 | -48 |
| 2009-05-21 | @ NYA | 41 | L 4-7 | 17-24 | 5 | 43,342 | Adam Eaton | Joba Chamberlain | Alfredo Aceves | Adam Eaton | Mariano Rivera | 201 | 252 | -51 |
| 2009-05-22 | @ WAS | 42 | W 4-2 | 18-24 | 5 | 22,556 | Rich Hill | Jordan Zimmermann | Danys Baez | Kip Wells | George Sherrill | 205 | 254 | -49 |
| 2009-05-23 | @ WAS | 43 | W 2-1 | 19-24 | 5 | 31,833 | Koji Uehara | Ross Detwiler | Brian Bass | Julian Tavarez | George Sherrill | 207 | 255 | -48 |
| 2009-05-24 | @ WAS | 44 | L 5-8 | 19-25 | 5 | 30,880 | Brad Bergesen | Shairon Martis | Ron Villone | Chris Ray | Joel Hanrahan | 212 | 263 | -51 |
| 2009-05-25 | vs TOR | 45 | W 4-1 | 20-25 | 4 | 24,904 | Jeremy Guthrie | Brian Tallet | Jeremy Guthrie | Brian Tallet | George Sherrill | 216 | 264 | -48 |
| 2009-05-26 | vs TOR | 46 | W 7-2 | 21-25 | 4 | 10,130 | Jason Berken | Ricky Romero | Jason Berken | Ricky Romero | Jim Johnson | 223 | 266 | -43 |
| 2009-05-27 | vs TOR | 47 | W 12-10 | 22-25 | 4 | 13,713 | Rich Hill | Roy Halladay | Danys Baez | Brian Wolfe | | 235 | 276 | -41 |
| 2009-05-28 | vs DET | 48 | W 5-1 | 23-25 | 4 | 11,937 | David Hernandez | Armando Galarraga | David Hernandez | Armando Galarraga | | 240 | 277 | -37 |
| 2009-05-29 | vs DET | 49 | W 7-2 | 24-25 | 4 | 42,704 | Brad Bergesen | Dontrelle Willis | Brad Bergesen | Dontrelle Willis | | 247 | 279 | -32 |
| 2009-05-30 | vs DET | 50 | L 3-6 | 24-26 | 4 | 34,567 | Jeremy Guthrie | Justin Verlander | Justin Verlander | Matt Albers | Fernando Rodney | 250 | 285 | -35 |
| 2009-05-31 | vs DET | 51 | L 0-3 | 24-27 | 4 | 32,233 | Jason Berken | Edwin Jackson | Edwin Jackson | Jason Berken | Fernando Rodney | 250 | 288 | -38 |
| 2009-06-01 | @ SEA | 52 | W 1-0 | 25-27 | 4 | 16,979 | Rich Hill | Jarrod Washburn | Rich Hill | Jarrod Washburn | George Sherrill | 251 | 288 | -37 |
| 2009-06-02 | @ SEA | 53 | L 2-8 | 25-28 | 4 | 17,978 | David Hernandez | Erik Bedard | Erik Bedard | David Hernandez | | 253 | 296 | -43 |
| 2009-06-03 | @ SEA | 54 | L 2-3 | 25-29 | 4 | 18,650 | Brad Bergesen | Jason Vargas | David Aardsma | Jim Johnson | | 255 | 299 | -44 |
| 2009-06-05 | @ OAK | 55 | L 1-9 | 25-30 | 5 | 12,608 | Jeremy Guthrie | Dallas Braden | Dallas Braden | Jeremy Guthrie | | 256 | 308 | -52 |
| 2009-06-06 | @ OAK | 56 | L 4-9 | 25-31 | 5 | 20,267 | Jason Berken | Trevor Cahill | Trevor Cahill | Jason Berken | | 260 | 317 | -57 |
| 2009-06-07 | @ OAK | 57 | L 0-3 | 25-32 | 5 | 17,208 | Rich Hill | Vin Mazzaro | Vin Mazzaro | Rich Hill | Andrew Bailey | 260 | 320 | -60 |
| 2009-06-09 | vs SEA | 58 | W 3-1 | 26-32 | 5 | 17,358 | Brad Bergesen | Jason Vargas | Brad Bergesen | Jason Vargas | George Sherrill | 263 | 321 | -58 |
| 2009-06-10 | vs SEA | 59 | L 1-4 | 26-33 | 5 | 12,770 | Jeremy Guthrie | Felix Hernandez | Felix Hernandez | Jeremy Guthrie | David Aardsma | 264 | 325 | -61 |
| 2009-06-11 | vs SEA | 60 | L 3-6 | 26-34 | 5 | 12,260 | Koji Uehara | Garrett Olson | Garrett Olson | Koji Uehara | David Aardsma | 267 | 331 | -64 |
| 2009-06-12 | vs ATL | 61 | L 2-7 | 26-35 | 5 | 28,469 | Jason Berken | Tommy Hanson | Tommy Hanson | Jason Berken | | 269 | 338 | -69 |
| 2009-06-13 | vs ATL | 62 | W 8-4 | 27-35 | 5 | 29,645 | Rich Hill | Kenshin Kawakami | Brian Bass | Eric O'Flaherty | | 277 | 342 | -65 |
| 2009-06-14 | vs ATL | 63 | W 11-2 | 27-36 | 5 | 26,770 | Brad Bergesen | Derek Lowe | Brad Bergesen | Derek Lowe | | 288 | 344 | -56 |
| 2009-06-16 | vs NYN | 64 | L 4-6 | 27-37 | 5 | 20,626 | Jeremy Guthrie | Mike Pelfrey | Mike Pelfrey | Jeremy Guthrie | Francisco Rodriguez | 292 | 350 | -58 |
| 2009-06-17 | vs NYN | 65 | W 6-4 | 28-37 | 5 | 31,906 | Koji Uehara | Tim Redding | Jim Johnson | Pedro Feliciano | George Sherrill | 298 | 354 | -56 |
| 2009-06-18 | vs NYN | 66 | W 5-4 | 29-37 | 5 | 23,009 | Jason Berken | Livan Hernandez | Matt Albers | Francisco Rodriguez | | 303 | 358 | -55 |
| 2009-06-19 | @ PHI | 67 | W 7-2 | 30-37 | 5 | 45,135 | Rich Hill | Antonio Bastardo | Rich Hill | Antonio Bastardo | | 310 | 360 | -50 |
| 2009-06-20 | @ PHI | 68 | W 6-5 | 31-37 | 5 | 44,939 | Brad Bergesen | J.A. Happ | Mark Hendrickson | Ryan Madson | George Sherrill | 316 | 365 | -49 |
| 2009-06-21 | @ PHI | 69 | W 2-1 | 32-37 | 5 | 45,256 | Jeremy Guthrie | Cole Hamels | Jeremy Guthrie | Cole Hamels | George Sherrill | 318 | 366 | -48 |
| 2009-06-23 | @ FLO | 70 | L 6-7 | 32-38 | 5 | 10,222 | Koji Uehara | Andrew Miller | Burke Badenhop | Brian Bass | | 324 | 373 | -49 |
| 2009-06-24 | @ FLO | 71 | L 2-5 | 32-39 | 5 | 12,469 | Jason Berken | Ricky Nolasco | Ricky Nolasco | Jason Berken | Dan Meyer | 326 | 378 | -52 |
| 2009-06-25 | @ FLO | 72 | L 3-11 | 33-39 | 5 | 12,822 | Rich Hill | Sean West | Sean West | Rich Hill | | 329 | 389 | -60 |
| 2009-06-26 | vs WAS | 73 | W 11-1 | 34-39 | 5 | 45,024 | Brad Bergesen | Ross Detwiler | Brad Bergesen | Ross Detwiler | | 340 | 390 | -50 |
| 2009-06-27 | vs WAS | 74 | W 6-3 | 35-39 | 5 | 39,633 | Jeremy Guthrie | Shairon Martis | Jeremy Guthrie | Shairon Martis | George Sherrill | 346 | 393 | -47 |
| 2009-06-28 | vs WAS | 75 | L 3-5 | 35-40 | 5 | 25,068 | David Hernandez | John Lannan | John Lannan | David Hernandez | Mike MacDougal | 349 | 398 | -49 |
| 2009-06-29 | vs BOS | 76 | L 0-4 | 35-41 | 5 | 36,548 | Jason Berken | Jon Lester | Jon Lester | Jason Berken | Jonathan Papelbon | 349 | 402 | -53 |
| 2009-06-30 | vs BOS | 77 | W 11-10 | 36-41 | 5 | 31,969 | Rich Hill | John Smoltz | Mark Hendrickson | Takashi Saito | George Sherrill | 360 | 412 | -52 |
| 2009-07-01 | vs BOS | 78 | L 5-6 | 36-42 | 5 | 29,391 | Brad Bergesen | Josh Beckett | Ramon Ramirez | Danys Baez | Jonathan Papelbon | 365 | 418 | -53 |
| 2009-07-02 | @ ANA | 79 | L 2-5 | 36-43 | 5 | 39,180 | Jeremy Guthrie | John Lackey | John Lackey | Jeremy Guthrie | Brian Fuentes | 367 | 423 | -56 |
| 2009-07-03 | @ ANA | 80 | W 6-4 | 37-43 | 5 | 39,104 | David Hernandez | Ervin Santana | David Hernandez | Ervin Santana | George Sherrill | 373 | 427 | -54 |
| 2009-07-04 | @ ANA | 81 | L 4-11 | 38-43 | 5 | 41,764 | Jason Berken | Sean O'Sullivan | Jason Bulger | Danys Baez | | 377 | 438 | -61 |
| 2009-07-05 | @ ANA | 82 | L 6-9 | 38-44 | 5 | 35,912 | Rich Hill | Joe Saunders | Darren Oliver | Matt Albers | Brian Fuentes | 383 | 447 | -64 |
| 2009-07-06 | @ SEA | 83 | L 0-5 | 38-45 | 5 | 24,018 | Brad Bergesen | Jarrod Washburn | Jarrod Washburn | Brad Bergesen | | 383 | 452 | -69 |
| 2009-07-07 | @ SEA | 84 | W 12-4 | 38-46 | 5 | 19,340 | Jeremy Guthrie | Erik Bedard | Mark Hendrickson | Chris Jakubauskas | | 395 | 456 | -61 |
| 2009-07-08 | @ SEA | 85 | W 5-3 | 39-46 | 5 | 27,040 | David Hernandez | Jason Vargas | Brian Bass | David Aardsma | George Sherrill | 400 | 459 | -59 |
| 2009-07-10 | vs TOR | 86 | L 0-2 | 39-47 | 5 | 30,574 | Jason Berken | Brett Cecil | Brett Cecil | Jason Berken | Scott Downs | 400 | 461 | -61 |
| 2009-07-11 | vs TOR | 87 | W 4-3 | 40-47 | 5 | 28,281 | Rich Hill | Ricky Romero | Mark Hendrickson | Jesse Carlson | | 404 | 464 | -60 |
| 2009-07-12 | vs TOR | 88 | W 4-2 | 41-47 | 5 | 21,621 | Brad Bergesen | Marc Rzepczynski | Brad Bergesen | Marc Rzepczynski | George Sherrill | 408 | 466 | -58 |
| 2009-07-17 | @ CHA | 89 | L 8-12 | 42-47 | 5 | 32,013 | Jason Berken | John Danks | John Danks | Jason Berken | | 416 | 478 | -62 |
| 2009-07-18 | @ CHA | 90 | L 3-4 | 42-48 | 5 | 32,881 | Brad Bergesen | Mark Buehrle | Mark Buehrle | Brad Bergesen | Bobby Jenks | 419 | 482 | -63 |
| 2009-07-19 | @ CHA | 91 | W 10-2 | 42-49 | 5 | 32,069 | Jeremy Guthrie | Jose Contreras | Jeremy Guthrie | Jose Contreras | | 429 | 484 | -55 |
| 2009-07-20 | @ NYA | 92 | L 1-2 | 42-50 | 5 | 46,342 | David Hernandez | Andy Pettitte | Alfredo Aceves | Jim Johnson | | 430 | 486 | -56 |
| 2009-07-21 | @ NYA | 93 | L 4-6 | 42-51 | 5 | 45,589 | Rich Hill | Sergio Mitre | Sergio Mitre | Rich Hill | Mariano Rivera | 434 | 492 | -58 |
| 2009-07-22 | @ NYA | 94 | L 4-6 | 42-52 | 5 | 47,134 | Jason Berken | A.J. Burnett | A.J. Burnett | Jason Berken | Mariano Rivera | 438 | 498 | -60 |
| 2009-07-24 | @ BOS | 95 | L 1-3 | 42-53 | 5 | 38,058 | Brad Bergesen | Brad Penny | Brad Penny | Brad Bergesen | Jonathan Papelbon | 439 | 501 | -62 |
| 2009-07-25 | @ BOS | 96 | L 2-7 | 42-54 | 5 | 38,063 | Jeremy Guthrie | Jon Lester | Jon Lester | Jeremy Guthrie | | 441 | 508 | -67 |
| 2009-07-26 | @ BOS | 97 | W 6-2 | 43-54 | 5 | 37,606 | David Hernandez | John Smoltz | David Hernandez | John Smoltz | | 447 | 510 | -63 |
| 2009-07-27 | vs KCA | 98 | L 3-5 | 43-55 | 5 | 15,169 | Rich Hill | Bruce Chen | Rob Tejeda | Matt Albers | Joakim Soria | 450 | 515 | -65 |
| 2009-07-28 | vs KCA | 99 | L 3-4 | 43-56 | 5 | 21,545 | Jason Berken | Brian Bannister | Jamey Wright | Danys Baez | Joakim Soria | 453 | 519 | -66 |
| 2009-07-29 | vs KCA | 100 | W 7-3 | 44-56 | 5 | 19,741 | Chris Tillman | Zack Greinke | Matt Albers | Rob Tejeda | Jim Johnson | 460 | 522 | -62 |
| 2009-07-30 | vs KCA | 101 | W 7-3 | 45-56 | 5 | 19,194 | Brad Bergesen | Luke Hochevar | Brad Bergesen | Luke Hochevar | | 467 | 525 | -58 |
| 2009-07-31 | vs BOS | 102 | L 5-6 | 45-57 | 5 | 44,091 | Jeremy Guthrie | John Smoltz | John Smoltz | Jeremy Guthrie | Jonathan Papelbon | 472 | 531 | -59 |
| 2009-08-01 | vs BOS | 103 | L 0-4 | 45-58 | 5 | 49,384 | David Hernandez | Josh Beckett | Josh Beckett | David Hernandez | | 472 | 535 | -63 |
| 2009-08-02 | vs BOS | 104 | L 10-18 | 45-59 | 5 | 43,115 | Jason Berken | Clay Buchholz | Manny Delcarmen | Jason Berken | | 482 | 553 | -71 |
| 2009-08-03 | @ DET | 105 | L 5-6 | 45-60 | 5 | 27,857 | Chris Tillman | Justin Verlander | Fernando Rodney | Danys Baez | | 487 | 559 | -72 |
| 2009-08-04 | @ DET | 106 | W 8-2 | 46-60 | 5 | 29,295 | Brian Matusz | Jarrod Washburn | Brian Matusz | Jarrod Washburn | | 495 | 561 | -66 |
| 2009-08-05 | @ DET | 107 | L 2-4 | 46-61 | 5 | 28,978 | Jeremy Guthrie | Edwin Jackson | Edwin Jackson | Jeremy Guthrie | Fernando Rodney | 497 | 565 | -68 |
| 2009-08-06 | @ DET | 108 | L 3-7 | 46-62 | 5 | 31,165 | David Hernandez | Rick Porcello | Rick Porcello | David Hernandez | Brandon Lyon | 500 | 572 | -72 |
| 2009-08-07 | @ TOR | 109 | W 7-5 | 47-62 | 5 | 30,795 | Jason Berken | Ricky Romero | Jason Berken | Ricky Romero | Jim Johnson | 507 | 577 | -70 |
| 2009-08-08 | @ TOR | 110 | L 2-3 | 47-63 | 5 | 28,613 | Chris Tillman | Brett Cecil | Jason Frasor | Danys Baez | | 509 | 580 | -71 |
| 2009-08-09 | @ TOR | 111 | L 3-7 | 47-64 | 5 | 27,464 | Brian Matusz | Roy Halladay | Roy Halladay | Brian Matusz | | 512 | 587 | -75 |
| 2009-08-10 | vs OAK | 112 | L 1-9 | 47-65 | 5 | 14,688 | Jeremy Guthrie | Gio Gonzalez | Gio Gonzalez | Jeremy Guthrie | | 513 | 596 | -83 |
| 2009-08-11 | vs OAK | 113 | W 3-2 | 48-65 | 5 | 23,006 | David Hernandez | Trevor Cahill | David Hernandez | Trevor Cahill | Jim Johnson | 516 | 598 | -82 |
| 2009-08-12 | vs OAK | 114 | L 3-6 | 48-66 | 5 | 19,128 | Jason Berken | Vin Mazzaro | Vin Mazzaro | Jason Berken | Andrew Bailey | 519 | 604 | -85 |
| 2009-08-14 | vs ANA | 115 | W 16-6 | 48-67 | 5 | 25,836 | Chris Tillman | Jered Weaver | Chris Tillman | Jered Weaver | | 535 | 610 | -75 |
| 2009-08-15 | vs ANA | 116 | L 1-5 | 48-68 | 5 | 28,770 | Brian Matusz | John Lackey | John Lackey | Brian Matusz | Brian Fuentes | 536 | 615 | -79 |
| 2009-08-16 | vs ANA | 117 | L 8-17 | 49-68 | 5 | 26,529 | Jeremy Guthrie | Sean O'Sullivan | Jason Bulger | Brian Bass | | 544 | 632 | -88 |
| 2009-08-17 | vs ANA | 118 | L 5-8 | 49-69 | 5 | 18,460 | David Hernandez | Ervin Santana | Ervin Santana | David Hernandez | Brian Fuentes | 549 | 640 | -91 |
| 2009-08-18 | @ TBA | 119 | L 4-5 | 49-70 | 5 | 16,514 | Jason Berken | David Price | David Price | Jason Berken | J.P. Howell | 553 | 645 | -92 |
| 2009-08-19 | @ TBA | 120 | L 1-3 | 49-71 | 5 | 18,474 | Chris Tillman | Jeff Niemann | Jeff Niemann | Chris Tillman | J.P. Howell | 554 | 648 | -94 |
| 2009-08-20 | @ TBA | 121 | W 8-7 | 50-71 | 5 | 15,870 | Brian Matusz | James Shields | Brian Matusz | James Shields | Jim Johnson | 562 | 655 | -93 |
| 2009-08-21 | @ CHA | 122 | W 5-1 | 51-71 | 5 | 34,125 | Jeremy Guthrie | Gavin Floyd | Jeremy Guthrie | Gavin Floyd | | 567 | 656 | -89 |
| 2009-08-22 | @ CHA | 123 | L 1-4 | 51-72 | 5 | 34,730 | David Hernandez | John Danks | John Danks | David Hernandez | Bobby Jenks | 568 | 660 | -92 |
| 2009-08-23 | @ CHA | 124 | W 5-4 | 52-72 | 5 | 32,742 | Jason Berken | Mark Buehrle | Jason Berken | Mark Buehrle | Jim Johnson | 573 | 664 | -91 |
| 2009-08-24 | @ MIN | 125 | L 1-2 | 52-73 | 5 | 20,271 | Chris Tillman | Scott Baker | Scott Baker | Chris Tillman | Joe Nathan | 574 | 666 | -92 |
| 2009-08-25 | @ MIN | 126 | L 6-7 | 52-74 | 5 | 23,696 | Brian Matusz | Armando Gabino | Jose Mijares | Kameron Mickolio | | 580 | 673 | -93 |
| 2009-08-26 | @ MIN | 127 | W 5-1 | 53-74 | 5 | 28,446 | Jeremy Guthrie | Nick Blackburn | Jeremy Guthrie | Nick Blackburn | | 585 | 674 | -89 |
| 2009-08-27 | vs CLE | 128 | L 4-5 | 53-75 | 5 | 13,991 | David Hernandez | Aaron Laffey | Rafael Perez | Jim Johnson | Kerry Wood | 589 | 679 | -90 |
| 2009-08-28 | vs CLE | 129 | W 13-4 | 53-76 | 5 | 13,961 | Jason Berken | Fausto Carmona | Jason Berken | Fausto Carmona | | 602 | 683 | -81 |
| 2009-08-29 | vs CLE | 130 | L 3-5 | 53-77 | 5 | 24,358 | Chris Tillman | Jeremy Sowers | Rafael Perez | Chris Ray | Chris Perez | 605 | 688 | -83 |
| 2009-08-30 | vs CLE | 131 | W 5-2 | 54-77 | 5 | 20,643 | Brian Matusz | Justin Masterson | Brian Matusz | Justin Masterson | Jim Johnson | 610 | 690 | -80 |
| 2009-08-31 | vs NYA | 132 | L 1-5 | 54-78 | 5 | 25,063 | Jeremy Guthrie | Andy Pettitte | Andy Pettitte | Jeremy Guthrie | Mariano Rivera | 611 | 695 | -84 |
| 2009-09-01 | vs NYA | 133 | L 6-9 | 54-79 | 6 | 25,782 | David Hernandez | A.J. Burnett | Damaso Marte | Chris Ray | Mariano Rivera | 617 | 704 | -87 |
| 2009-09-02 | vs NYA | 134 | L 2-10 | 55-79 | 5 | 21,126 | Jason Berken | CC Sabathia | CC Sabathia | Kameron Mickolio | Phil Hughes | 619 | 714 | -95 |
| 2009-09-04 | vs TEX | 135 | L 1-5 | 55-80 | 5 | 15,557 | Chris Tillman | Scott Feldman | Scott Feldman | Chris Tillman | Neftali Feliz | 620 | 719 | -99 |
| 2009-09-05 | vs TEX | 136 | W 5-4 | 56-80 | 5 | 18,028 | Brian Matusz | Kevin Millwood | Brian Matusz | Kevin Millwood | Jim Johnson | 625 | 723 | -98 |
| 2009-09-06 | vs TEX | 137 | W 7-0 | 57-80 | 5 | 21,599 | Jeremy Guthrie | Derek Holland | Jeremy Guthrie | Derek Holland | | 632 | 723 | -91 |
| 2009-09-08 | @ BOS | 138 | L 0-10 | 57-81 | 5 | 37,647 | David Hernandez | Clay Buchholz | Clay Buchholz | David Hernandez | | 632 | 733 | -101 |
| 2009-09-09 | @ BOS | 139 | L 5-7 | 57-82 | 5 | 37,712 | Jason Berken | Paul Byrd | Billy Wagner | Matt Albers | Jonathan Papelbon | 637 | 740 | -103 |
| 2009-09-11 | @ NYA | 140 | W 10-4 | 57-83 | 5 | 46,771 | Chris Tillman | Andy Pettitte | Chris Tillman | Damaso Marte | Mark Hendrickson | 647 | 744 | -97 |
| 2009-09-12 | @ NYA | 141 | W 7-3 | 58-83 | 5 | 46,497 | Brian Matusz | A.J. Burnett | Brian Matusz | A.J. Burnett | | 654 | 747 | -93 |
| 2009-09-13 | @ NYA | 142 | L 3-13 | 59-83 | 7 | 46,413 | Jeremy Guthrie | CC Sabathia | CC Sabathia | Jeremy Guthrie | | 657 | 760 | -103 |
| 2009-09-14 | vs TBA | 143 | L 4-8 | 59-84 | 5 | 10,628 | David Hernandez | David Price | David Price | David Hernandez | | 661 | 768 | -107 |
| 2009-09-15 | vs TBA | 144 | W 10-5 | 59-85 | 5 | 11,575 | Jason Berken | Jeff Niemann | Jason Berken | Jeff Niemann | | 671 | 773 | -102 |
| 2009-09-16 | vs TBA | 145 | W 4-2 | 60-85 | 5 | 10,548 | Chris Tillman | Andy Sonnanstine | Jim Johnson | Russ Springer | | 675 | 775 | -100 |
| 2009-09-17 | vs TBA | 146 | L 0-3 | 60-86 | 5 | 12,436 | Mark Hendrickson | Wade Davis | Wade Davis | Mark Hendrickson | | 675 | 778 | -103 |
| 2009-09-18 | vs BOS | 147 | L 1-3 | 60-87 | 5 | 26,812 | Jeremy Guthrie | Clay Buchholz | Clay Buchholz | Jeremy Guthrie | Jonathan Papelbon | 676 | 781 | -105 |
| 2009-09-19 | vs BOS | 148 | L 5-11 | 61-87 | 5 | 39,285 | David Hernandez | Jon Lester | Jon Lester | Matt Albers | | 681 | 792 | -111 |
| 2009-09-20 | vs BOS | 149 | L 3-9 | 61-88 | 5 | 27,546 | Jason Berken | Daisuke Matsuzaka | Daisuke Matsuzaka | Jason Berken | | 684 | 801 | -117 |
| 2009-09-21 | @ TOR | 150 | L 2-9 | 61-89 | 5 | 11,598 | Chris Tillman | David Purcey | David Purcey | Chris Tillman | | 686 | 810 | -124 |
| 2009-09-22 | @ TOR | 151 | L 5-6 | 61-90 | 5 | 11,869 | Mark Hendrickson | Brian Tallet | Shawn Camp | Dennis Sarfate | | 691 | 816 | -125 |
| 2009-09-23 | @ TOR | 152 | L 3-7 | 61-91 | 5 | 13,743 | Jeremy Guthrie | Scott Richmond | Scott Richmond | Jeremy Guthrie | | 694 | 823 | -129 |
| 2009-09-25 | @ CLE | 153 | L 2-4 | 61-92 | 5 | 33,472 | David Hernandez | Fausto Carmona | Fausto Carmona | David Hernandez | Kerry Wood | 696 | 827 | -131 |
| 2009-09-26 | @ CLE | 154 | L 8-9 | 61-93 | 5 | 31,749 | Jason Berken | Jeremy Sowers | Kerry Wood | Jim Johnson | | 704 | 836 | -132 |
| 2009-09-27 | @ CLE | 155 | L 0-9 | 61-94 | 5 | 29,930 | Chris Tillman | David Huff | David Huff | Chris Tillman | | 704 | 845 | -141 |
| 2009-09-28 | @ TBA | 156 | L 6-7 | 61-95 | 5 | 10,352 | Mark Hendrickson | Jeff Niemann | Lance Cormier | Chris Ray | Grant Balfour | 710 | 852 | -142 |
| 2009-09-29 | @ TBA | 157 | L 1-3 | 61-96 | 5 | 10,349 | Jeremy Guthrie | Wade Davis | Wade Davis | Jeremy Guthrie | Grant Balfour | 711 | 855 | -144 |
| 2009-09-30 | @ TBA | 158 | L 3-5 | 61-97 | 5 | 10,554 | David Hernandez | James Shields | James Shields | David Hernandez | Russ Springer | 714 | 860 | -146 |
| 2009-10-01 | @ TBA | 159 | W 3-2 | 62-97 | 5 | 10,716 | Chris Waters | Matt Garza | Chris Waters | Matt Garza | Jim Johnson | 717 | 862 | -145 |
| 2009-10-02 | vs TOR | 160 | W 13-7 | 62-98 | 5 | 16,921 | Jason Berken | David Purcey | Jason Berken | David Purcey | | 730 | 869 | -139 |
| 2009-10-03 | vs TOR | 161 | W 6-3 | 63-98 | 5 | 23,254 | Mark Hendrickson | Scott Richmond | Mark Hendrickson | Scott Richmond | Jim Johnson | 736 | 872 | -136 |
| 2009-10-04 | vs TOR | 162 | W 5-4 | 64-98 | 5 | 17,969 | Jeremy Guthrie | Ricky Romero | Matt Albers | Brandon League | | 741 | 876 | -135 |