| 1999-04-06 | vs TOR | 1 | W 6-1 | 1-0 | 1 | 45,601 | Brad Radke | Pat Hentgen | Brad Radke | Pat Hentgen | | 6 | 1 | 5 |
| 1999-04-07 | vs TOR | 2 | L 3-9 | 1-1 | 2 | 9,220 | Mike Lincoln | David Wells | David Wells | Mike Lincoln | Roy Halladay | 9 | 10 | -1 |
| 1999-04-08 | vs TOR | 3 | W 11-9 | 1-2 | 2 | 9,431 | Eric Milton | Joey Hamilton | Mike Trombley | Joey Hamilton | Rick Aguilera | 20 | 19 | 1 |
| 1999-04-09 | vs CLE | 4 | L 5-14 | 2-2 | 4 | 16,348 | LaTroy Hawkins | Charles Nagy | Charles Nagy | LaTroy Hawkins | | 25 | 33 | -8 |
| 1999-04-10 | vs CLE | 5 | L 7-12 | 3-2 | 1 | 18,829 | Benj Sampson | Dwight Gooden | Steve Karsay | Mike Lincoln | | 32 | 45 | -13 |
| 1999-04-11 | vs CLE | 6 | L 8-9 | 3-3 | 3 | 12,430 | Brad Radke | Jaret Wright | Jaret Wright | Brad Radke | Michael Jackson | 40 | 54 | -14 |
| 1999-04-12 | @ DET | 7 | W 1-0 | 4-3 | 2 | 47,449 | Eric Milton | Willie Blair | Rick Aguilera | Sean Runyan | | 41 | 54 | -13 |
| 1999-04-14 | @ DET | 8 | L 1-7 | 4-4 | 3 | 12,263 | LaTroy Hawkins | Jeff Weaver | Jeff Weaver | LaTroy Hawkins | | 42 | 61 | -19 |
| 1999-04-15 | @ DET | 9 | W 8-6 | 5-4 | 1 | 11,818 | Benj Sampson | Brian Moehler | Bob Wells | Brian Moehler | Rick Aguilera | 50 | 67 | -17 |
| 1999-04-17 | @ CLE | 10 | L 1-5 | 5-6 | 5 | 40,582 | Brad Radke | Charles Nagy | Charles Nagy | Brad Radke | | 51 | 72 | -21 |
| 1999-04-17 | @ CLE | 11 | W 13-8 | 5-6 | 5 | 42,860 | Eric Milton | Jaret Wright | Rick Aguilera | Michael Jackson | | 64 | 80 | -16 |
| 1999-04-18 | @ CLE | 12 | L 2-3 | 5-7 | 4 | 42,317 | Mike Lincoln | Dave Burba | Paul Shuey | Bob Wells | Michael Jackson | 66 | 83 | -17 |
| 1999-04-19 | @ KCA | 13 | W 6-4 | 6-7 | 3 | 11,919 | LaTroy Hawkins | Jeff Suppan | LaTroy Hawkins | Jeff Suppan | Rick Aguilera | 72 | 87 | -15 |
| 1999-04-20 | @ KCA | 14 | W 8-7 | 7-7 | 4 | 11,217 | Benj Sampson | Jim Pittsley | Rick Aguilera | Jay Witasick | | 80 | 94 | -14 |
| 1999-04-21 | @ KCA | 15 | L 2-3 | 7-8 | 4 | 10,826 | Brad Radke | Kevin Appier | Terry Mathews | Eddie Guardado | | 82 | 97 | -15 |
| 1999-04-22 | vs TEX | 16 | L 4-6 | 7-9 | 4 | 11,221 | Eric Milton | Aaron Sele | Aaron Sele | Eric Milton | John Wetteland | 86 | 103 | -17 |
| 1999-04-23 | vs TEX | 17 | L 2-4 | 7-10 | 4 | 15,321 | Mike Lincoln | Mark Clark | Mark Clark | Mike Lincoln | John Wetteland | 88 | 107 | -19 |
| 1999-04-24 | vs TEX | 18 | L 2-7 | 7-11 | 4 | 19,479 | LaTroy Hawkins | Mike Morgan | Mike Morgan | LaTroy Hawkins | | 90 | 114 | -24 |
| 1999-04-25 | vs TEX | 19 | L 5-9 | 7-12 | 5 | 14,801 | Dan Perkins | Rick Helling | Rick Helling | Dan Perkins | | 95 | 123 | -28 |
| 1999-04-26 | vs BOS | 20 | W 6-2 | 8-12 | 4 | 9,674 | Brad Radke | Tim Wakefield | Brad Radke | Tim Wakefield | Mike Trombley | 101 | 125 | -24 |
| 1999-04-27 | vs BOS | 21 | W 6-5 | 9-12 | 4 | 10,681 | Eric Milton | Mark Portugal | Eddie Guardado | Jim Corsi | Rick Aguilera | 107 | 130 | -23 |
| 1999-04-28 | vs BOS | 22 | L 4-9 | 9-13 | 5 | 11,097 | Mike Lincoln | Pat Rapp | Pat Rapp | Mike Lincoln | | 111 | 139 | -28 |
| 1999-04-30 | @ BAL | 23 | L 1-7 | 9-14 | 4 | 41,688 | LaTroy Hawkins | Sidney Ponson | Sidney Ponson | LaTroy Hawkins | | 112 | 146 | -34 |
| 1999-05-01 | @ BAL | 24 | W 7-2 | 10-14 | 4 | 44,054 | Brad Radke | Rocky Coppinger | Brad Radke | Rocky Coppinger | | 119 | 148 | -29 |
| 1999-05-02 | @ BAL | 25 | L 0-6 | 10-15 | 4 | 41,535 | Eric Milton | Mike Mussina | Mike Mussina | Eric Milton | | 119 | 154 | -35 |
| 1999-05-04 | vs NYA | 26 | W 8-5 | 11-15 | 4 | 15,923 | Mike Lincoln | Ramiro Mendoza | Mike Lincoln | Ramiro Mendoza | Rick Aguilera | 127 | 159 | -32 |
| 1999-05-05 | vs NYA | 27 | L 3-5 | 11-16 | 4 | 17,859 | LaTroy Hawkins | Andy Pettitte | Andy Pettitte | LaTroy Hawkins | Mariano Rivera | 130 | 164 | -34 |
| 1999-05-06 | vs NYA | 28 | L 3-4 | 11-17 | 4 | 16,465 | Brad Radke | David Cone | Jason Grimsley | Rick Aguilera | Mariano Rivera | 133 | 168 | -35 |
| 1999-05-07 | vs KCA | 29 | L 1-5 | 11-18 | 5 | 16,417 | Eric Milton | Kevin Appier | Kevin Appier | Eric Milton | | 134 | 173 | -39 |
| 1999-05-08 | vs KCA | 30 | L 2-6 | 11-19 | 5 | 17,052 | Dan Perkins | Jose Rosado | Jose Rosado | Dan Perkins | Jose Santiago | 136 | 179 | -43 |
| 1999-05-09 | vs KCA | 31 | L 2-7 | 11-20 | 5 | 11,581 | Mike Lincoln | Jeff Suppan | Jeff Suppan | Mike Lincoln | | 138 | 186 | -48 |
| 1999-05-10 | vs KCA | 32 | L 4-8 | 11-21 | 5 | 9,636 | LaTroy Hawkins | Jay Witasick | Jay Witasick | LaTroy Hawkins | | 142 | 194 | -52 |
| 1999-05-11 | @ TBA | 33 | W 2-1 | 12-21 | 5 | 17,227 | Brad Radke | Ryan Rupe | Brad Radke | Ryan Rupe | Rick Aguilera | 144 | 195 | -51 |
| 1999-05-12 | @ TBA | 34 | W 9-4 | 13-21 | 5 | 18,068 | Eric Milton | Rolando Arrojo | Eric Milton | Rolando Arrojo | Mike Trombley | 153 | 199 | -46 |
| 1999-05-14 | @ OAK | 35 | L 5-7 | 13-22 | 5 | 8,145 | Mike Lincoln | Tom Candiotti | Tim Worrell | Mike Lincoln | Billy Taylor | 158 | 206 | -48 |
| 1999-05-15 | @ OAK | 36 | L 5-6 | 13-23 | 5 | 18,016 | LaTroy Hawkins | Mike Oquist | T.J. Mathews | Eddie Guardado | | 163 | 212 | -49 |
| 1999-05-16 | @ OAK | 37 | L 2-4 | 13-24 | 5 | 31,804 | Brad Radke | Jimmy Haynes | Jimmy Haynes | Brad Radke | Billy Taylor | 165 | 216 | -51 |
| 1999-05-17 | @ SEA | 38 | L 5-15 | 14-24 | 5 | 25,710 | Eric Milton | Mac Suzuki | John Halama | Eric Milton | | 170 | 231 | -61 |
| 1999-05-18 | @ SEA | 39 | L 1-10 | 14-25 | 5 | 20,486 | Dan Perkins | Freddy Garcia | Freddy Garcia | Dan Perkins | | 171 | 241 | -70 |
| 1999-05-19 | @ SEA | 40 | L 0-7 | 14-26 | 5 | 20,497 | Mike Lincoln | Jeff Fassero | Jeff Fassero | Mike Lincoln | | 171 | 248 | -77 |
| 1999-05-21 | vs OAK | 41 | W 2-1 | 15-26 | 5 | 14,433 | LaTroy Hawkins | Jimmy Haynes | Travis Miller | Doug Jones | | 173 | 249 | -76 |
| 1999-05-22 | vs OAK | 42 | W 2-1 | 16-26 | 6 | 15,381 | Brad Radke | Kenny Rogers | Bob Wells | Brad Rigby | | 175 | 250 | -75 |
| 1999-05-23 | vs OAK | 43 | W 8-3 | 17-26 | 5 | 12,881 | Eric Milton | Gil Heredia | Eric Milton | Gil Heredia | | 183 | 253 | -70 |
| 1999-05-24 | vs SEA | 44 | W 10-5 | 17-27 | 5 | 12,101 | Dan Perkins | Jeff Fassero | Dan Perkins | Jeff Fassero | | 193 | 258 | -65 |
| 1999-05-25 | vs SEA | 45 | L 5-15 | 18-27 | 5 | 13,875 | Gary Rath | John Halama | John Halama | Gary Rath | | 198 | 273 | -75 |
| 1999-05-26 | vs SEA | 46 | L 3-11 | 19-27 | 4 | 17,022 | LaTroy Hawkins | Jamie Moyer | Jamie Moyer | LaTroy Hawkins | | 201 | 284 | -83 |
| 1999-05-28 | @ TEX | 47 | L 4-6 | 19-28 | 4 | 27,765 | Brad Radke | Aaron Sele | Aaron Sele | Brad Radke | John Wetteland | 205 | 290 | -85 |
| 1999-05-29 | @ TEX | 48 | L 3-4 | 19-29 | 4 | 38,466 | Eric Milton | John Burkett | John Wetteland | Mike Trombley | | 208 | 294 | -86 |
| 1999-05-30 | @ TEX | 49 | L 2-3 | 19-30 | 4 | 40,286 | Dan Perkins | Mark Clark | Jeff Zimmerman | Joe Mays | John Wetteland | 210 | 297 | -87 |
| 1999-05-31 | @ ANA | 50 | W 3-2 | 20-30 | 4 | 20,466 | LaTroy Hawkins | Tim Belcher | LaTroy Hawkins | Shigetoshi Hasegawa | Mike Trombley | 213 | 299 | -86 |
| 1999-06-01 | @ ANA | 51 | L 1-5 | 20-31 | 4 | 17,003 | Mike Lincoln | Ken Hill | Ken Hill | Mike Lincoln | | 214 | 304 | -90 |
| 1999-06-02 | @ ANA | 52 | L 1-2 | 20-32 | 4 | 17,766 | Brad Radke | Chuck Finley | Chuck Finley | Brad Radke | Troy Percival | 215 | 306 | -91 |
| 1999-06-04 | vs HOU | 53 | L 6-7 | 20-33 | 4 | 13,152 | Eric Milton | Mike Hampton | Mike Hampton | Mike Trombley | Billy Wagner | 221 | 313 | -92 |
| 1999-06-05 | vs HOU | 54 | L 5-6 | 20-34 | 4 | 17,150 | Dan Perkins | Chris Holt | Scott Elarton | Joe Mays | Billy Wagner | 226 | 319 | -93 |
| 1999-06-06 | vs HOU | 55 | W 13-6 | 20-35 | 4 | 13,720 | LaTroy Hawkins | Sean Bergman | Benj Sampson | Sean Bergman | | 239 | 325 | -86 |
| 1999-06-07 | vs CIN | 56 | W 8-6 | 21-35 | 4 | 12,241 | Mike Lincoln | Steve Avery | Mike Lincoln | Steve Avery | Mike Trombley | 247 | 331 | -84 |
| 1999-06-08 | vs CIN | 57 | W 5-2 | 22-35 | 4 | 13,157 | Brad Radke | Ron Villone | Brad Radke | Ron Villone | Mike Trombley | 252 | 333 | -81 |
| 1999-06-09 | vs CIN | 58 | L 1-3 | 22-36 | 4 | 11,047 | Eric Milton | Brett Tomko | Brett Tomko | Eric Milton | Danny Graves | 253 | 336 | -83 |
| 1999-06-11 | @ MIL | 59 | W 9-7 | 23-36 | 4 | 30,344 | Dan Perkins | Scott Karl | Bob Wells | David Weathers | Mike Trombley | 262 | 343 | -81 |
| 1999-06-12 | @ MIL | 60 | W 8-6 | 24-36 | 4 | 23,915 | LaTroy Hawkins | Cal Eldred | Benj Sampson | Cal Eldred | Mike Trombley | 270 | 349 | -79 |
| 1999-06-14 | @ BOS | 61 | L 3-4 | 24-37 | 4 | 30,099 | Brad Radke | Jin Ho Cho | John Wasdin | Mike Trombley | | 273 | 353 | -80 |
| 1999-06-15 | @ BOS | 62 | L 2-4 | 24-38 | 4 | 31,805 | Eric Milton | Pedro Martinez | Pedro Martinez | Eric Milton | Tim Wakefield | 275 | 357 | -82 |
| 1999-06-16 | @ BOS | 63 | L 1-5 | 24-39 | 4 | 30,085 | Dan Perkins | Brian Rose | Brian Rose | Dan Perkins | Mark Guthrie | 276 | 362 | -86 |
| 1999-06-17 | @ BOS | 64 | W 8-7 | 25-39 | 4 | 31,446 | LaTroy Hawkins | Pat Rapp | LaTroy Hawkins | Pat Rapp | Mike Trombley | 284 | 369 | -85 |
| 1999-06-18 | vs TBA | 65 | W 8-5 | 26-39 | 4 | 24,157 | Mike Lincoln | Mickey Callaway | Bob Wells | Scott Aldred | Mike Trombley | 292 | 374 | -82 |
| 1999-06-19 | vs TBA | 66 | L 3-4 | 26-40 | 4 | 16,823 | Brad Radke | Bryan Rekar | Bryan Rekar | Brad Radke | Roberto Hernandez | 295 | 378 | -83 |
| 1999-06-20 | vs TBA | 67 | L 5-6 | 26-41 | 4 | 15,413 | Eric Milton | Wilson Alvarez | Alan Newman | Mike Trombley | | 300 | 384 | -84 |
| 1999-06-21 | vs TBA | 68 | L 2-3 | 26-42 | 4 | 13,878 | Joe Mays | Ryan Rupe | Ryan Rupe | Rob Radlosky | Roberto Hernandez | 302 | 387 | -85 |
| 1999-06-22 | @ CHA | 69 | L 1-6 | 26-43 | 4 | 12,428 | LaTroy Hawkins | Jim Parque | Jim Parque | LaTroy Hawkins | | 303 | 393 | -90 |
| 1999-06-23 | @ CHA | 70 | W 12-10 | 27-43 | 4 | 14,770 | Mike Lincoln | Mike Sirotka | Benj Sampson | Mike Sirotka | Mike Trombley | 315 | 403 | -88 |
| 1999-06-24 | @ CHA | 71 | L 3-5 | 27-44 | 4 | 13,246 | Brad Radke | Jaime Navarro | Jaime Navarro | Brad Radke | Bob Howry | 318 | 408 | -90 |
| 1999-06-25 | @ DET | 72 | L 0-2 | 27-45 | 4 | 21,604 | Eric Milton | Brian Moehler | Brian Moehler | Eric Milton | | 318 | 410 | -92 |
| 1999-06-26 | @ DET | 73 | W 1-0 | 28-45 | 4 | 19,667 | Joe Mays | Dave Mlicki | Joe Mays | Dave Mlicki | Mike Trombley | 319 | 410 | -91 |
| 1999-06-27 | @ DET | 74 | W 12-7 | 28-46 | 4 | 21,355 | LaTroy Hawkins | Jeff Weaver | LaTroy Hawkins | Jeff Weaver | | 331 | 417 | -86 |
| 1999-06-29 | @ CLE | 75 | L 4-5 | 28-47 | 4 | 43,159 | Brad Radke | Dave Burba | Steve Reed | Mike Trombley | | 335 | 422 | -87 |
| 1999-06-30 | @ CLE | 76 | W 5-3 | 29-47 | 4 | 43,061 | Eric Milton | Jaret Wright | Eric Milton | Jaret Wright | Mike Trombley | 340 | 425 | -85 |
| 1999-07-01 | @ CLE | 77 | L 5-7 | 29-48 | 4 | 43,010 | Joe Mays | Bartolo Colon | Bartolo Colon | Hector Carrasco | Michael Jackson | 345 | 432 | -87 |
| 1999-07-02 | vs DET | 78 | W 11-4 | 29-49 | 5 | 12,033 | LaTroy Hawkins | Jeff Weaver | LaTroy Hawkins | Jeff Weaver | | 356 | 436 | -80 |
| 1999-07-03 | vs DET | 79 | W 7-2 | 30-49 | 5 | 14,042 | Mike Lincoln | Nelson Cruz | Mike Lincoln | Nelson Cruz | | 363 | 438 | -75 |
| 1999-07-04 | vs DET | 80 | L 5-15 | 31-49 | 4 | 13,094 | Dan Perkins | Justin Thompson | Justin Thompson | Dan Perkins | | 368 | 453 | -85 |
| 1999-07-06 | vs CLE | 81 | L 1-3 | 31-50 | 4 | 12,579 | Eric Milton | Jaret Wright | Jaret Wright | Eric Milton | Michael Jackson | 369 | 456 | -87 |
| 1999-07-07 | vs CLE | 82 | W 4-3 | 32-50 | 4 | 12,710 | Joe Mays | Bartolo Colon | Mike Trombley | Steve Reed | | 373 | 459 | -86 |
| 1999-07-08 | vs CLE | 83 | L 2-9 | 32-51 | 4 | 14,118 | Mike Lincoln | Charles Nagy | Charles Nagy | Mike Lincoln | | 375 | 468 | -93 |
| 1999-07-09 | vs PIT | 84 | W 5-4 | 33-51 | 4 | 13,427 | Brad Radke | Jose Silva | Brad Radke | Jose Silva | Mike Trombley | 380 | 472 | -92 |
| 1999-07-10 | vs PIT | 85 | W 5-4 | 34-51 | 4 | 14,865 | LaTroy Hawkins | Jason Schmidt | Eddie Guardado | Mike Williams | | 385 | 476 | -91 |
| 1999-07-11 | vs PIT | 86 | L 2-10 | 35-51 | 4 | 18,587 | Joe Mays | Todd Ritchie | Todd Ritchie | Joe Mays | | 387 | 486 | -99 |
| 1999-07-15 | @ CHN | 87 | L 3-9 | 35-52 | 4 | 39,420 | Brad Radke | Dan Serafini | Scott Sanders | Brad Radke | Terry Adams | 390 | 495 | -105 |
| 1999-07-16 | @ CHN | 88 | L 10-11 | 35-53 | 4 | 39,249 | Eric Milton | Jon Lieber | Terry Adams | Mike Trombley | | 400 | 506 | -106 |
| 1999-07-17 | @ CHN | 89 | W 8-0 | 36-53 | 4 | 39,044 | Joe Mays | Terry Mulholland | Joe Mays | Terry Mulholland | | 408 | 506 | -98 |
| 1999-07-18 | @ SLN | 90 | W 5-2 | 37-53 | 4 | 45,665 | LaTroy Hawkins | Darren Oliver | LaTroy Hawkins | Darren Oliver | | 413 | 508 | -95 |
| 1999-07-19 | @ SLN | 91 | L 4-8 | 37-54 | 4 | 37,408 | Mike Lincoln | Kent Mercker | Kent Mercker | Mike Lincoln | Ricky Bottalico | 417 | 516 | -99 |
| 1999-07-20 | @ SLN | 92 | W 4-2 | 38-54 | 4 | 35,257 | Brad Radke | Larry Luebbers | Brad Radke | Larry Luebbers | Mike Trombley | 421 | 518 | -97 |
| 1999-07-21 | vs CHA | 93 | L 3-6 | 38-55 | 4 | 12,399 | Eric Milton | Jaime Navarro | Bill Simas | Hector Carrasco | Bob Howry | 424 | 524 | -100 |
| 1999-07-22 | vs CHA | 94 | W 3-0 | 39-55 | 4 | 12,397 | Joe Mays | James Baldwin | Joe Mays | James Baldwin | Mike Trombley | 427 | 524 | -97 |
| 1999-07-23 | vs SEA | 95 | W 5-4 | 40-55 | 4 | 20,014 | LaTroy Hawkins | John Halama | Hector Carrasco | Jose Paniagua | | 432 | 528 | -96 |
| 1999-07-24 | vs SEA | 96 | W 10-3 | 40-56 | 4 | 30,138 | Mark Redman | Gil Meche | Bob Wells | Gil Meche | | 442 | 531 | -89 |
| 1999-07-25 | vs SEA | 97 | L 3-4 | 40-57 | 4 | 21,621 | Brad Radke | Jamie Moyer | Jamie Moyer | Brad Radke | Jose Mesa | 445 | 535 | -90 |
| 1999-07-26 | vs OAK | 98 | L 7-14 | 41-57 | 4 | 11,356 | Eric Milton | Gil Heredia | Buddy Groom | Benj Sampson | | 452 | 549 | -97 |
| 1999-07-27 | vs OAK | 99 | W 3-2 | 42-57 | 4 | 11,582 | Joe Mays | Tim Hudson | Joe Mays | Billy Taylor | Eddie Guardado | 455 | 551 | -96 |
| 1999-07-28 | vs OAK | 100 | W 5-3 | 43-57 | 4 | 20,420 | LaTroy Hawkins | Jimmy Haynes | LaTroy Hawkins | Jimmy Haynes | Mike Trombley | 460 | 554 | -94 |
| 1999-07-30 | @ ANA | 101 | W 3-1 | 44-57 | 4 | 38,319 | Brad Radke | Ken Hill | Brad Radke | Ken Hill | | 463 | 555 | -92 |
| 1999-07-31 | @ ANA | 102 | W 8-0 | 45-57 | 4 | 37,011 | Eric Milton | Chuck Finley | Eric Milton | Chuck Finley | | 471 | 555 | -84 |
| 1999-08-01 | @ ANA | 103 | L 1-2 | 45-58 | 4 | 24,045 | Joe Mays | Steve Sparks | Steve Sparks | Joe Mays | Troy Percival | 472 | 557 | -85 |
| 1999-08-02 | @ TEX | 104 | L 4-5 | 45-59 | 4 | 24,720 | LaTroy Hawkins | John Burkett | Jeff Zimmerman | Eddie Guardado | John Wetteland | 476 | 562 | -86 |
| 1999-08-03 | @ TEX | 105 | L 5-9 | 45-60 | 4 | 28,090 | Benj Sampson | Mike Morgan | Mike Morgan | Benj Sampson | | 481 | 571 | -90 |
| 1999-08-04 | @ TEX | 106 | L 1-3 | 45-61 | 4 | 29,224 | Brad Radke | Esteban Loaiza | Esteban Loaiza | Brad Radke | John Wetteland | 482 | 574 | -92 |
| 1999-08-06 | @ KCA | 107 | W 9-8 | 46-61 | 4 | 23,471 | Eric Milton | Dan Reichert | Travis Miller | Scott Service | Mike Trombley | 491 | 582 | -91 |
| 1999-08-07 | @ KCA | 108 | W 6-5 | 47-61 | 4 | 38,391 | Joe Mays | Jose Rosado | Bob Wells | Brad Rigby | Mike Trombley | 497 | 587 | -90 |
| 1999-08-08 | @ KCA | 109 | W 7-3 | 48-61 | 4 | 15,595 | LaTroy Hawkins | Blake Stein | LaTroy Hawkins | Brad Rigby | Hector Carrasco | 504 | 590 | -86 |
| 1999-08-10 | vs TOR | 110 | L 6-10 | 49-61 | 4 | 15,842 | Brad Radke | Kelvim Escobar | Kelvim Escobar | Brad Radke | | 510 | 600 | -90 |
| 1999-08-11 | vs TOR | 111 | L 3-6 | 49-62 | 4 | 15,777 | Eric Milton | Chris Carpenter | Chris Carpenter | Eric Milton | | 513 | 606 | -93 |
| 1999-08-12 | vs TOR | 112 | W 3-0 | 50-62 | 4 | 21,206 | Joe Mays | Pat Hentgen | Joe Mays | Pat Hentgen | Mike Trombley | 516 | 606 | -90 |
| 1999-08-13 | @ NYA | 113 | L 2-14 | 51-62 | 5 | 44,568 | LaTroy Hawkins | Andy Pettitte | Andy Pettitte | LaTroy Hawkins | | 518 | 620 | -102 |
| 1999-08-14 | @ NYA | 114 | W 6-3 | 52-62 | 3 | 55,179 | Dan Perkins | David Cone | Bob Wells | David Cone | Mike Trombley | 524 | 623 | -99 |
| 1999-08-15 | @ NYA | 115 | W 5-3 | 53-62 | 3 | 56,180 | Brad Radke | Hideki Irabu | Brad Radke | Hideki Irabu | Mike Trombley | 529 | 626 | -97 |
| 1999-08-16 | @ NYA | 116 | L 0-2 | 53-63 | 3 | 36,503 | Eric Milton | Roger Clemens | Roger Clemens | Eric Milton | Mariano Rivera | 529 | 628 | -99 |
| 1999-08-17 | @ BAL | 117 | L 3-8 | 53-64 | 4 | 40,485 | Joe Mays | Mike Mussina | Mike Mussina | Joe Mays | | 532 | 636 | -104 |
| 1999-08-18 | @ BAL | 118 | L 0-2 | 53-65 | 4 | 38,820 | LaTroy Hawkins | Scott Erickson | Scott Erickson | LaTroy Hawkins | | 532 | 638 | -106 |
| 1999-08-19 | @ BAL | 119 | L 3-9 | 53-66 | 4 | 38,320 | Dan Perkins | Jason Johnson | Jason Johnson | Dan Perkins | | 535 | 647 | -112 |
| 1999-08-20 | vs NYA | 120 | L 3-9 | 53-67 | 4 | 23,595 | Brad Radke | Hideki Irabu | Hideki Irabu | Brad Radke | Jeff Nelson | 538 | 656 | -118 |
| 1999-08-21 | vs NYA | 121 | W 6-1 | 54-67 | 5 | 32,170 | Eric Milton | Roger Clemens | Eric Milton | Roger Clemens | Eddie Guardado | 544 | 657 | -113 |
| 1999-08-22 | vs NYA | 122 | L 3-5 | 54-68 | 4 | 26,150 | Joe Mays | Orlando Hernandez | Orlando Hernandez | Joe Mays | Mariano Rivera | 547 | 662 | -115 |
| 1999-08-23 | vs BOS | 123 | L 1-4 | 54-69 | 4 | 14,331 | LaTroy Hawkins | Pat Rapp | Pat Rapp | LaTroy Hawkins | Derek Lowe | 548 | 666 | -118 |
| 1999-08-24 | vs BOS | 124 | L 1-7 | 54-70 | 4 | 12,332 | Jason Ryan | Pedro Martinez | Pedro Martinez | Jason Ryan | | 549 | 673 | -124 |
| 1999-08-25 | vs BOS | 125 | W 6-3 | 55-70 | 3 | 11,185 | Brad Radke | Mark Portugal | Brad Radke | Mark Portugal | | 555 | 676 | -121 |
| 1999-08-27 | vs KCA | 126 | W 4-1 | 56-70 | 3 | 11,176 | Eric Milton | Jose Rosado | Eric Milton | Jose Rosado | Mike Trombley | 559 | 677 | -118 |
| 1999-08-28 | vs KCA | 127 | W 4-3 | 57-70 | 3 | 14,136 | Joe Mays | Mac Suzuki | Bob Wells | Alvin Morman | | 563 | 680 | -117 |
| 1999-08-29 | vs KCA | 128 | W 6-2 | 58-70 | 3 | 11,585 | LaTroy Hawkins | Blake Stein | LaTroy Hawkins | Blake Stein | Bob Wells | 569 | 682 | -113 |
| 1999-08-30 | @ TOR | 129 | L 1-2 | 58-71 | 5 | 22,137 | Jason Ryan | Pat Hentgen | Pat Hentgen | Jason Ryan | Billy Koch | 570 | 684 | -114 |
| 1999-08-31 | @ TOR | 130 | W 14-3 | 58-72 | 4 | 23,136 | Brad Radke | Joey Hamilton | Brad Radke | Joey Hamilton | | 584 | 687 | -103 |
| 1999-09-01 | @ TOR | 131 | L 0-4 | 58-73 | 4 | 23,145 | Eric Milton | Kelvim Escobar | Kelvim Escobar | Eric Milton | | 584 | 691 | -107 |
| 1999-09-02 | @ TOR | 132 | L 1-6 | 58-74 | 4 | 22,255 | Joe Mays | David Wells | David Wells | Joe Mays | | 585 | 697 | -112 |
| 1999-09-03 | @ TBA | 133 | L 2-4 | 58-75 | 4 | 15,355 | LaTroy Hawkins | Bobby Witt | Norm Charlton | Eddie Guardado | Roberto Hernandez | 587 | 701 | -114 |
| 1999-09-04 | @ TBA | 134 | L 3-11 | 59-75 | 4 | 17,805 | Jason Ryan | Wilson Alvarez | Albie Lopez | Travis Miller | | 590 | 712 | -122 |
| 1999-09-05 | @ TBA | 135 | W 4-1 | 60-75 | 4 | 17,480 | Brad Radke | Ryan Rupe | Brad Radke | Ryan Rupe | | 594 | 713 | -119 |
| 1999-09-06 | @ TBA | 136 | W 13-7 | 60-76 | 5 | 16,929 | Eric Milton | Dan Wheeler | Hector Carrasco | Rick White | | 607 | 720 | -113 |
| 1999-09-07 | vs BAL | 137 | L 0-5 | 60-77 | 4 | 9,263 | Joe Mays | Scott Erickson | Scott Erickson | Joe Mays | | 607 | 725 | -118 |
| 1999-09-08 | vs BAL | 138 | L 0-10 | 60-78 | 4 | 9,564 | LaTroy Hawkins | Jason Johnson | Jason Johnson | LaTroy Hawkins | | 607 | 735 | -128 |
| 1999-09-09 | vs BAL | 139 | L 5-6 | 60-79 | 4 | 9,903 | Jason Ryan | Matt Riley | Alberto Reyes | Travis Miller | Mike Timlin | 612 | 741 | -129 |
| 1999-09-10 | vs ANA | 140 | L 2-4 | 60-80 | 4 | 11,200 | Brad Radke | Chuck Finley | Chuck Finley | Brad Radke | Troy Percival | 614 | 745 | -131 |
| 1999-09-11 | vs ANA | 141 | W 7-0 | 61-80 | 4 | 11,222 | Eric Milton | Ramon Ortiz | Eric Milton | Ramon Ortiz | | 621 | 745 | -124 |
| 1999-09-12 | vs ANA | 142 | L 3-6 | 61-81 | 4 | 11,301 | Joe Mays | Jarrod Washburn | Jarrod Washburn | Joe Mays | | 624 | 751 | -127 |
| 1999-09-13 | vs ANA | 143 | L 5-6 | 61-82 | 4 | 8,716 | LaTroy Hawkins | Brian Cooper | Mike Magnante | LaTroy Hawkins | Shigetoshi Hasegawa | 629 | 757 | -128 |
| 1999-09-14 | vs TEX | 144 | L 4-5 | 61-83 | 4 | 9,717 | Jason Ryan | Jeff Fassero | Danny Kolb | Eddie Guardado | John Wetteland | 633 | 762 | -129 |
| 1999-09-15 | vs TEX | 145 | L 3-8 | 61-84 | 4 | 9,706 | Brad Radke | Esteban Loaiza | Esteban Loaiza | Brad Radke | | 636 | 770 | -134 |
| 1999-09-17 | @ SEA | 146 | L 3-4 | 61-85 | 4 | 44,315 | Eric Milton | John Halama | Paul Abbott | Mike Trombley | | 639 | 774 | -135 |
| 1999-09-18 | @ SEA | 147 | L 0-5 | 61-86 | 4 | 44,511 | Joe Mays | Gil Meche | Gil Meche | Joe Mays | | 639 | 779 | -140 |
| 1999-09-19 | @ SEA | 148 | W 2-1 | 62-86 | 4 | 44,362 | LaTroy Hawkins | Jamie Moyer | LaTroy Hawkins | Jamie Moyer | Mike Trombley | 641 | 780 | -139 |
| 1999-09-20 | @ OAK | 149 | W 4-0 | 63-86 | 4 | 6,512 | Jason Ryan | Kevin Appier | Jason Ryan | Kevin Appier | | 645 | 780 | -135 |
| 1999-09-21 | @ OAK | 150 | L 3-5 | 63-87 | 4 | 6,498 | Brad Radke | Mike Oquist | Ron Mahay | Hector Carrasco | Jason Isringhausen | 648 | 785 | -137 |
| 1999-09-22 | @ OAK | 151 | W 5-4 | 64-87 | 4 | 9,895 | Eric Milton | Tim Hudson | Mark Redman | Tim Worrell | Mike Trombley | 653 | 789 | -136 |
| 1999-09-24 | vs CHA | 152 | W 6-2 | 65-87 | 4 | 11,308 | Joe Mays | Aaron Myette | Joe Mays | Aaron Myette | | 659 | 791 | -132 |
| 1999-09-25 | vs CHA | 153 | L 4-13 | 66-87 | 4 | 26,324 | LaTroy Hawkins | Mike Sirotka | Mike Sirotka | LaTroy Hawkins | | 663 | 804 | -141 |
| 1999-09-26 | vs CHA | 154 | L 0-3 | 66-88 | 4 | 11,947 | Jason Ryan | James Baldwin | James Baldwin | Jason Ryan | Bob Howry | 663 | 807 | -144 |
| 1999-09-27 | vs CHA | 155 | L 1-3 | 66-89 | 4 | 9,022 | Brad Radke | Kip Wells | Bill Simas | Bob Wells | Keith Foulke | 664 | 810 | -146 |
| 1999-09-28 | vs DET | 156 | L 4-7 | 66-90 | 4 | 11,875 | Eric Milton | Willie Blair | Matt Anderson | Mike Trombley | Todd Jones | 668 | 817 | -149 |
| 1999-09-29 | vs DET | 157 | L 3-6 | 66-91 | 5 | 9,933 | Joe Mays | Dave Mlicki | Dave Mlicki | Joe Mays | Todd Jones | 671 | 823 | -152 |
| 1999-09-30 | vs DET | 158 | L 5-6 | 66-92 | 4 | 11,464 | LaTroy Hawkins | C.J. Nitkowski | Francisco Cordero | Bob Wells | Todd Jones | 676 | 829 | -153 |
| 1999-10-01 | @ CHA | 159 | L 8-9 | 66-93 | 4 | 11,887 | Jason Ryan | James Baldwin | James Baldwin | Jason Ryan | Bob Howry | 684 | 838 | -154 |
| 1999-10-02 | @ CHA | 160 | L 1-6 | 66-94 | 4 | 17,904 | Dan Perkins | Kip Wells | Kip Wells | Dan Perkins | | 685 | 844 | -159 |
| 1999-10-03 | @ CHA | 161 | L 1-1 | 66-95 | 4 | 18,694 | Eric Milton | Tanyon Sturtze | | | | 686 | 845 | -159 |