| 1999-04-05 | @ SEA | 1 | W 8-2 | 1-0 | 1 | 51,656 | James Baldwin | Jeff Fassero | James Baldwin | Jeff Fassero | | 8 | 2 | 6 |
| 1999-04-06 | @ SEA | 2 | W 11-3 | 1-1 | 2 | 20,435 | Jim Parque | Jamie Moyer | Jim Parque | Jamie Moyer | | 19 | 5 | 14 |
| 1999-04-07 | @ SEA | 3 | L 3-7 | 1-2 | 3 | 21,050 | John Snyder | Freddy Garcia | Freddy Garcia | John Snyder | Jose Mesa | 22 | 12 | 10 |
| 1999-04-09 | vs KCA | 4 | L 5-10 | 2-2 | 1 | 26,243 | Mike Sirotka | Brian Barber | Brian Barber | Mike Sirotka | | 27 | 22 | 5 |
| 1999-04-10 | vs KCA | 5 | L 4-9 | 2-3 | 2 | 11,908 | Jaime Navarro | Jim Pittsley | Jim Pittsley | Jaime Navarro | Scott Service | 31 | 31 | 0 |
| 1999-04-11 | vs KCA | 6 | L 1-3 | 2-4 | 4 | 10,503 | James Baldwin | Kevin Appier | Kevin Appier | James Baldwin | Jeff Montgomery | 32 | 34 | -2 |
| 1999-04-13 | @ BOS | 7 | L 0-6 | 2-5 | 4 | 31,874 | Jim Parque | Bret Saberhagen | Bret Saberhagen | Jim Parque | | 32 | 40 | -8 |
| 1999-04-15 | @ BOS | 8 | W 4-0 | 3-5 | 4 | 22,461 | John Snyder | Pedro Martinez | John Snyder | Pedro Martinez | | 36 | 40 | -4 |
| 1999-04-16 | @ KCA | 9 | L 2-7 | 3-6 | 5 | 11,326 | Mike Sirotka | Kevin Appier | Kevin Appier | Mike Sirotka | | 38 | 47 | -9 |
| 1999-04-17 | @ KCA | 10 | W 6-5 | 4-6 | 6 | 11,766 | Jaime Navarro | Jose Rosado | Sean Lowe | Jeff Montgomery | Bob Howry | 44 | 52 | -8 |
| 1999-04-18 | @ KCA | 11 | W 7-5 | 5-6 | 3 | 18,529 | James Baldwin | Brian Barber | James Baldwin | Brian Barber | Bob Howry | 51 | 57 | -6 |
| 1999-04-20 | vs SEA | 12 | W 3-1 | 6-6 | 3 | 8,980 | Jim Parque | Jeff Fassero | Jim Parque | Jeff Fassero | Bob Howry | 54 | 58 | -4 |
| 1999-04-21 | vs SEA | 13 | W 2-1 | 7-6 | 3 | 9,405 | John Snyder | Jamie Moyer | John Snyder | Jose Paniagua | Bob Howry | 56 | 59 | -3 |
| 1999-04-23 | vs DET | 14 | W 5-0 | 8-6 | 2 | 9,837 | Mike Sirotka | Willie Blair | Mike Sirotka | Willie Blair | | 61 | 59 | 2 |
| 1999-04-24 | vs DET | 15 | W 3-1 | 9-6 | 2 | 11,264 | Jaime Navarro | Dave Mlicki | Jaime Navarro | Dave Mlicki | Bob Howry | 64 | 60 | 4 |
| 1999-04-25 | vs DET | 16 | L 4-9 | 9-7 | 2 | 15,370 | James Baldwin | Jeff Weaver | Jeff Weaver | James Baldwin | | 68 | 69 | -1 |
| 1999-04-28 | vs TBA | 17 | W 10-7 | 9-8 | 4 | 0 | Jim Parque | Bryan Rekar | Jim Parque | Bryan Rekar | Bob Howry | 78 | 76 | 2 |
| 1999-04-28 | vs TBA | 18 | W 9-1 | 9-8 | 4 | 10,300 | John Snyder | Tony Saunders | John Snyder | Tony Saunders | | 87 | 77 | 10 |
| 1999-04-29 | vs TBA | 19 | L 1-4 | 10-9 | 3 | 10,022 | Mike Sirotka | Wilson Alvarez | Wilson Alvarez | Mike Sirotka | Roberto Hernandez | 88 | 81 | 7 |
| 1999-04-30 | @ ANA | 20 | L 1-3 | 10-10 | 3 | 35,053 | Jaime Navarro | Steve Sparks | Mark Petkovsek | Jaime Navarro | Troy Percival | 89 | 84 | 5 |
| 1999-05-01 | @ ANA | 21 | W 8-5 | 11-10 | 3 | 35,296 | James Baldwin | Chuck Finley | David Lundquist | Troy Percival | Bob Howry | 97 | 89 | 8 |
| 1999-05-02 | @ ANA | 22 | L 3-6 | 11-11 | 3 | 34,737 | Jim Parque | Omar Olivares | Omar Olivares | Jim Parque | | 100 | 95 | 5 |
| 1999-05-03 | @ ANA | 23 | W 8-1 | 12-11 | 3 | 31,995 | John Snyder | Tim Belcher | John Snyder | Tim Belcher | | 108 | 96 | 12 |
| 1999-05-04 | @ BAL | 24 | L 5-9 | 12-12 | 3 | 37,846 | Mike Sirotka | Scott Erickson | Mike Timlin | David Lundquist | | 113 | 105 | 8 |
| 1999-05-05 | @ BAL | 25 | L 0-8 | 12-13 | 3 | 40,081 | Jaime Navarro | Juan Guzman | Juan Guzman | Jaime Navarro | | 113 | 113 | 0 |
| 1999-05-06 | @ BAL | 26 | L 2-4 | 12-14 | 3 | 36,880 | James Baldwin | Sidney Ponson | Sidney Ponson | James Baldwin | Mike Timlin | 115 | 117 | -2 |
| 1999-05-07 | vs OAK | 27 | W 7-1 | 13-14 | 3 | 11,181 | Jim Parque | Tom Candiotti | Jim Parque | Tom Candiotti | | 122 | 118 | 4 |
| 1999-05-08 | vs OAK | 28 | W 5-3 | 14-14 | 3 | 15,489 | John Snyder | Jimmy Haynes | John Snyder | Jimmy Haynes | Bob Howry | 127 | 121 | 6 |
| 1999-05-09 | vs OAK | 29 | L 0-3 | 14-15 | 3 | 12,652 | Mike Sirotka | Mike Oquist | Mike Oquist | Mike Sirotka | Doug Jones | 127 | 124 | 3 |
| 1999-05-10 | vs TEX | 30 | W 5-2 | 15-15 | 3 | 12,670 | Jaime Navarro | Rick Helling | Jaime Navarro | Rick Helling | | 132 | 126 | 6 |
| 1999-05-11 | vs TEX | 31 | L 5-11 | 16-15 | 3 | 10,905 | James Baldwin | Esteban Loaiza | Jeff Zimmerman | Bob Howry | | 137 | 137 | 0 |
| 1999-05-14 | @ NYA | 32 | W 8-2 | 17-15 | 3 | 33,793 | Jim Parque | Orlando Hernandez | Jim Parque | Orlando Hernandez | Bill Simas | 145 | 139 | 6 |
| 1999-05-15 | @ NYA | 33 | W 12-4 | 17-16 | 3 | 45,824 | John Snyder | Ramiro Mendoza | John Snyder | Ramiro Mendoza | | 157 | 143 | 14 |
| 1999-05-16 | @ NYA | 34 | L 1-2 | 17-17 | 3 | 51,046 | Mike Sirotka | Andy Pettitte | Andy Pettitte | Mike Sirotka | Mariano Rivera | 158 | 145 | 13 |
| 1999-05-17 | vs CLE | 35 | L 9-13 | 18-17 | 3 | 17,101 | Jaime Navarro | Bartolo Colon | Bartolo Colon | Jaime Navarro | | 167 | 158 | 9 |
| 1999-05-18 | vs CLE | 36 | L 0-13 | 18-18 | 3 | 13,429 | James Baldwin | Dwight Gooden | Dwight Gooden | James Baldwin | | 167 | 171 | -4 |
| 1999-05-19 | vs CLE | 37 | L 7-13 | 19-18 | 3 | 14,854 | Jim Parque | Charles Nagy | Charles Nagy | Jim Parque | | 174 | 184 | -10 |
| 1999-05-22 | vs NYA | 38 | L 2-10 | 20-18 | 4 | 0 | John Snyder | Roger Clemens | Roger Clemens | John Snyder | | 176 | 194 | -18 |
| 1999-05-22 | vs NYA | 39 | W 2-1 | 20-18 | 4 | 35,310 | Mike Sirotka | Andy Pettitte | Mike Sirotka | Andy Pettitte | Bill Simas | 178 | 195 | -17 |
| 1999-05-23 | vs NYA | 40 | L 7-8 | 21-19 | 3 | 22,845 | Jaime Navarro | David Cone | Mariano Rivera | Bill Simas | | 185 | 203 | -18 |
| 1999-05-24 | @ CLE | 41 | W 10-3 | 21-20 | 3 | 43,208 | James Baldwin | Dwight Gooden | Sean Lowe | Dwight Gooden | | 195 | 206 | -11 |
| 1999-05-25 | @ CLE | 42 | L 1-3 | 21-21 | 3 | 42,161 | Jim Parque | Charles Nagy | Charles Nagy | Jim Parque | Michael Jackson | 196 | 209 | -13 |
| 1999-05-26 | @ CLE | 43 | L 2-6 | 21-22 | 3 | 43,228 | Mike Sirotka | Dave Burba | Dave Burba | Mike Sirotka | Paul Shuey | 198 | 215 | -17 |
| 1999-05-27 | @ DET | 44 | L 5-10 | 22-22 | 3 | 13,465 | John Snyder | Jeff Weaver | Jeff Weaver | John Snyder | | 203 | 225 | -22 |
| 1999-05-28 | @ DET | 45 | W 9-1 | 23-22 | 3 | 20,437 | Jaime Navarro | Justin Thompson | Jaime Navarro | Justin Thompson | | 212 | 226 | -14 |
| 1999-05-29 | @ DET | 46 | W 7-1 | 24-22 | 2 | 27,821 | James Baldwin | Brian Moehler | James Baldwin | Brian Moehler | | 219 | 227 | -8 |
| 1999-05-30 | @ DET | 47 | L 2-3 | 24-23 | 3 | 20,263 | Jim Parque | Dave Mlicki | Dave Mlicki | Jim Parque | Todd Jones | 221 | 230 | -9 |
| 1999-06-01 | @ TOR | 48 | W 6-2 | 25-23 | 2 | 20,399 | Mike Sirotka | Kelvim Escobar | Mike Sirotka | Kelvim Escobar | | 227 | 232 | -5 |
| 1999-06-02 | @ TOR | 49 | L 7-9 | 25-24 | 2 | 22,197 | John Snyder | Chris Carpenter | Chris Carpenter | John Snyder | Billy Koch | 234 | 241 | -7 |
| 1999-06-03 | @ TOR | 50 | W 10-3 | 25-25 | 3 | 33,673 | Jaime Navarro | Pat Hentgen | Jaime Navarro | Pat Hentgen | | 244 | 244 | 0 |
| 1999-06-04 | vs PIT | 51 | L 3-6 | 25-26 | 3 | 12,238 | James Baldwin | Francisco Cordova | Marc Wilkins | Bill Simas | | 247 | 250 | -3 |
| 1999-06-05 | vs PIT | 52 | W 6-5 | 26-26 | 3 | 20,066 | Jim Parque | Kris Benson | Jim Parque | Kris Benson | Keith Foulke | 253 | 255 | -2 |
| 1999-06-06 | vs PIT | 53 | W 4-3 | 27-26 | 2 | 26,827 | Mike Sirotka | Jose Silva | Mike Sirotka | Jose Silva | Bob Howry | 257 | 258 | -1 |
| 1999-06-07 | vs HOU | 54 | L 2-8 | 27-27 | 3 | 16,881 | John Snyder | Jose Lima | Jose Lima | John Snyder | | 259 | 266 | -7 |
| 1999-06-08 | vs HOU | 55 | W 4-3 | 28-27 | 2 | 11,836 | Jaime Navarro | Shane Reynolds | Jaime Navarro | Shane Reynolds | Bob Howry | 263 | 269 | -6 |
| 1999-06-09 | vs HOU | 56 | L 4-13 | 29-27 | 2 | 12,138 | James Baldwin | Mike Hampton | Mike Hampton | James Baldwin | | 267 | 282 | -15 |
| 1999-06-11 | @ CHN | 57 | W 5-3 | 30-27 | 2 | 38,989 | Jim Parque | Jon Lieber | Jim Parque | Jon Lieber | | 272 | 285 | -13 |
| 1999-06-12 | @ CHN | 58 | W 8-2 | 31-27 | 2 | 38,146 | Mike Sirotka | Steve Trachsel | Mike Sirotka | Steve Trachsel | | 280 | 287 | -7 |
| 1999-06-13 | @ CHN | 59 | W 6-4 | 32-27 | 2 | 38,071 | Jaime Navarro | Kevin Tapani | Bill Simas | Rick Aguilera | Keith Foulke | 286 | 291 | -5 |
| 1999-06-14 | vs TBA | 60 | W 9-7 | 33-27 | 2 | 15,457 | John Snyder | Wilson Alvarez | John Snyder | Wilson Alvarez | Bob Howry | 295 | 298 | -3 |
| 1999-06-15 | vs TBA | 61 | L 2-3 | 33-28 | 2 | 11,347 | James Baldwin | Ryan Rupe | Ryan Rupe | James Baldwin | Roberto Hernandez | 297 | 301 | -4 |
| 1999-06-16 | vs TBA | 62 | W 3-2 | 34-28 | 2 | 10,903 | Jim Parque | Bobby Witt | Sean Lowe | Norm Charlton | | 300 | 303 | -3 |
| 1999-06-17 | vs BAL | 63 | W 9-3 | 35-28 | 2 | 16,496 | Mike Sirotka | Juan Guzman | Mike Sirotka | Juan Guzman | Keith Foulke | 309 | 306 | 3 |
| 1999-06-18 | vs BAL | 64 | L 2-3 | 35-29 | 2 | 17,098 | Jaime Navarro | Mike Mussina | Mike Mussina | Jaime Navarro | | 311 | 309 | 2 |
| 1999-06-19 | vs BAL | 65 | L 9-11 | 36-29 | 2 | 30,232 | John Snyder | Scott Erickson | Arthur Rhodes | Keith Foulke | Scott Kamieniecki | 320 | 320 | 0 |
| 1999-06-20 | vs BAL | 66 | L 4-8 | 36-30 | 2 | 22,755 | James Baldwin | Jason Johnson | Jason Johnson | James Baldwin | Mike Timlin | 324 | 328 | -4 |
| 1999-06-22 | vs MIN | 67 | W 6-1 | 37-30 | 2 | 12,428 | Jim Parque | LaTroy Hawkins | Jim Parque | LaTroy Hawkins | | 330 | 329 | 1 |
| 1999-06-23 | vs MIN | 68 | L 10-12 | 37-31 | 2 | 14,770 | Mike Sirotka | Mike Lincoln | Benj Sampson | Mike Sirotka | Mike Trombley | 340 | 341 | -1 |
| 1999-06-24 | vs MIN | 69 | W 5-3 | 38-31 | 2 | 13,246 | Jaime Navarro | Brad Radke | Jaime Navarro | Brad Radke | Bob Howry | 345 | 344 | 1 |
| 1999-06-25 | @ BOS | 70 | L 1-6 | 38-32 | 2 | 31,097 | John Snyder | Jin Ho Cho | Jin Ho Cho | John Snyder | Mark Guthrie | 346 | 350 | -4 |
| 1999-06-26 | @ BOS | 71 | L 1-17 | 38-33 | 2 | 32,758 | James Baldwin | Pedro Martinez | Pedro Martinez | James Baldwin | John Wasdin | 347 | 367 | -20 |
| 1999-06-27 | @ BOS | 72 | W 7-6 | 39-33 | 2 | 30,627 | Jim Parque | Brian Rose | Bill Simas | Tim Wakefield | Bob Howry | 354 | 373 | -19 |
| 1999-06-28 | @ BOS | 73 | L 1-14 | 39-34 | 2 | 24,616 | Mike Sirotka | Bret Saberhagen | Bret Saberhagen | Mike Sirotka | | 355 | 387 | -32 |
| 1999-06-29 | @ KCA | 74 | L 4-7 | 39-35 | 2 | 15,027 | Jaime Navarro | Kevin Appier | Kevin Appier | Jaime Navarro | Scott Service | 359 | 394 | -35 |
| 1999-06-30 | @ KCA | 75 | W 10-9 | 39-36 | 2 | 14,026 | John Snyder | Jeff Suppan | Bob Howry | Scott Service | | 369 | 403 | -34 |
| 1999-07-01 | @ KCA | 76 | W 6-2 | 40-36 | 2 | 18,697 | James Baldwin | Mac Suzuki | James Baldwin | Marc Pisciotta | | 375 | 405 | -30 |
| 1999-07-02 | vs BOS | 77 | L 1-6 | 40-37 | 2 | 23,266 | Jim Parque | Pedro Martinez | Pedro Martinez | Jim Parque | | 376 | 411 | -35 |
| 1999-07-03 | vs BOS | 78 | W 11-2 | 40-38 | 3 | 18,028 | Mike Sirotka | Brian Rose | Mike Sirotka | Brian Rose | | 387 | 413 | -26 |
| 1999-07-04 | vs BOS | 79 | L 2-5 | 40-39 | 2 | 16,495 | Jaime Navarro | Bret Saberhagen | Bret Saberhagen | Jaime Navarro | Tim Wakefield | 389 | 418 | -29 |
| 1999-07-06 | vs KCA | 80 | L 7-8 | 40-40 | 2 | 11,251 | James Baldwin | Jeff Suppan | Matt Whisenant | Keith Foulke | | 396 | 426 | -30 |
| 1999-07-07 | vs KCA | 81 | W 7-1 | 41-40 | 2 | 11,963 | Jim Parque | Mac Suzuki | Jim Parque | Mac Suzuki | | 403 | 427 | -24 |
| 1999-07-08 | vs KCA | 82 | W 6-5 | 42-40 | 2 | 14,738 | Pat Daneker | Jose Rosado | Keith Foulke | Tim Byrdak | | 409 | 432 | -23 |
| 1999-07-09 | vs CHN | 83 | W 3-2 | 43-40 | 2 | 44,153 | Mike Sirotka | Kevin Tapani | Bob Howry | Terry Adams | | 412 | 434 | -22 |
| 1999-07-10 | vs CHN | 84 | L 2-10 | 44-40 | 2 | 44,008 | Jaime Navarro | Jon Lieber | Jon Lieber | Jaime Navarro | | 414 | 444 | -30 |
| 1999-07-11 | vs CHN | 85 | L 3-6 | 44-41 | 2 | 43,115 | James Baldwin | Steve Trachsel | Steve Trachsel | James Baldwin | Terry Adams | 417 | 450 | -33 |
| 1999-07-15 | @ SLN | 86 | L 2-3 | 44-42 | 2 | 40,258 | Mike Sirotka | Jose Jimenez | Rich Croushore | Todd Rizzo | | 419 | 453 | -34 |
| 1999-07-16 | @ SLN | 87 | W 9-8 | 45-42 | 2 | 46,909 | Jaime Navarro | Juan Acevedo | Jaime Navarro | Juan Acevedo | Bob Howry | 428 | 461 | -33 |
| 1999-07-17 | @ SLN | 88 | L 6-8 | 45-43 | 2 | 48,650 | James Baldwin | Kent Bottenfield | Garrett Stephenson | Bryan Ward | Ricky Bottalico | 434 | 469 | -35 |
| 1999-07-18 | @ MIL | 89 | L 4-5 | 45-44 | 2 | 27,295 | Jim Parque | Bill Pulsipher | Eric Plunk | Todd Rizzo | | 438 | 474 | -36 |
| 1999-07-19 | @ MIL | 90 | W 10-8 | 45-45 | 2 | 33,250 | Pat Daneker | Kyle Peterson | Bill Simas | Rocky Coppinger | Keith Foulke | 448 | 482 | -34 |
| 1999-07-20 | @ MIL | 91 | L 4-5 | 45-46 | 2 | 20,342 | Mike Sirotka | Steve Woodard | Eric Plunk | Sean Lowe | Bob Wickman | 452 | 487 | -35 |
| 1999-07-21 | @ MIN | 92 | W 6-3 | 46-46 | 2 | 12,399 | Jaime Navarro | Eric Milton | Bill Simas | Hector Carrasco | Bob Howry | 458 | 490 | -32 |
| 1999-07-22 | @ MIN | 93 | L 0-3 | 46-47 | 2 | 12,397 | James Baldwin | Joe Mays | Joe Mays | James Baldwin | Mike Trombley | 458 | 493 | -35 |
| 1999-07-23 | vs TOR | 94 | L 1-2 | 46-48 | 2 | 14,166 | Jim Parque | Joey Hamilton | Joey Hamilton | Jim Parque | Billy Koch | 459 | 495 | -36 |
| 1999-07-24 | vs TOR | 95 | W 6-5 | 47-48 | 2 | 25,674 | John Snyder | Kelvim Escobar | Scott Eyre | Kelvim Escobar | Bob Howry | 465 | 500 | -35 |
| 1999-07-25 | vs TOR | 96 | L 3-11 | 48-48 | 2 | 18,299 | Mike Sirotka | Chris Carpenter | Chris Carpenter | Mike Sirotka | | 468 | 511 | -43 |
| 1999-07-26 | vs TOR | 97 | L 3-4 | 48-49 | 2 | 17,631 | Jaime Navarro | Pat Hentgen | John Frascatore | Bob Howry | Billy Koch | 471 | 515 | -44 |
| 1999-07-27 | vs NYA | 98 | L 3-5 | 48-50 | 2 | 21,364 | James Baldwin | Orlando Hernandez | Orlando Hernandez | James Baldwin | Mariano Rivera | 474 | 520 | -46 |
| 1999-07-28 | vs NYA | 99 | W 11-3 | 48-51 | 2 | 22,523 | Jim Parque | Andy Pettitte | Carlos Castillo | Andy Pettitte | | 485 | 523 | -38 |
| 1999-07-29 | vs NYA | 100 | W 5-1 | 49-51 | 2 | 24,056 | John Snyder | David Cone | John Snyder | David Cone | Keith Foulke | 490 | 524 | -34 |
| 1999-07-30 | @ CLE | 101 | L 2-10 | 50-51 | 2 | 43,181 | Mike Sirotka | Bartolo Colon | Bartolo Colon | Mike Sirotka | | 492 | 534 | -42 |
| 1999-07-31 | @ CLE | 102 | L 10-13 | 50-52 | 2 | 43,209 | Jaime Navarro | Dave Burba | Paul Shuey | Carlos Castillo | Michael Jackson | 502 | 547 | -45 |
| 1999-08-01 | @ CLE | 103 | W 6-3 | 51-52 | 2 | 43,067 | James Baldwin | Charles Nagy | James Baldwin | Charles Nagy | Bob Howry | 508 | 550 | -42 |
| 1999-08-02 | @ DET | 104 | W 6-2 | 52-52 | 2 | 26,637 | Kip Wells | Brian Moehler | Kip Wells | Brian Moehler | | 514 | 552 | -38 |
| 1999-08-03 | @ DET | 105 | W 9-6 | 53-52 | 2 | 24,484 | John Snyder | Justin Thompson | John Snyder | Justin Thompson | Bob Howry | 523 | 558 | -35 |
| 1999-08-05 | @ OAK | 106 | L 6-7 | 53-53 | 2 | 9,305 | Mike Sirotka | Omar Olivares | T.J. Mathews | Scott Eyre | | 529 | 565 | -36 |
| 1999-08-06 | @ OAK | 107 | L 1-9 | 53-54 | 2 | 11,267 | Jaime Navarro | Gil Heredia | Gil Heredia | Jaime Navarro | | 530 | 574 | -44 |
| 1999-08-07 | @ OAK | 108 | L 1-11 | 53-55 | 2 | 26,091 | Jim Parque | Kevin Appier | Kevin Appier | Jim Parque | | 531 | 585 | -54 |
| 1999-08-08 | @ OAK | 109 | L 5-7 | 53-56 | 2 | 22,821 | James Baldwin | Tim Hudson | Doug Jones | Keith Foulke | | 536 | 592 | -56 |
| 1999-08-09 | @ SEA | 110 | L 4-6 | 53-57 | 2 | 42,978 | John Snyder | Gil Meche | Gil Meche | John Snyder | Jose Mesa | 540 | 598 | -58 |
| 1999-08-10 | @ SEA | 111 | L 3-4 | 53-58 | 2 | 43,696 | Mike Sirotka | Jamie Moyer | Jamie Moyer | Bob Howry | | 543 | 602 | -59 |
| 1999-08-11 | @ SEA | 112 | L 2-11 | 54-58 | 2 | 45,194 | Jaime Navarro | Paul Abbott | Paul Abbott | Jaime Navarro | | 545 | 613 | -68 |
| 1999-08-13 | vs TEX | 113 | W 4-2 | 55-58 | 3 | 0 | Kip Wells | John Burkett | Kip Wells | John Burkett | Bob Howry | 549 | 615 | -66 |
| 1999-08-13 | vs TEX | 114 | W 7-4 | 55-58 | 3 | 20,444 | James Baldwin | Ryan Glynn | James Baldwin | Ryan Glynn | | 556 | 619 | -63 |
| 1999-08-14 | vs TEX | 115 | W 8-7 | 57-58 | 2 | 27,476 | Jim Parque | Mike Morgan | Bob Howry | Jeff Zimmerman | | 564 | 626 | -62 |
| 1999-08-15 | vs TEX | 116 | L 0-10 | 57-59 | 2 | 22,708 | John Snyder | Esteban Loaiza | Esteban Loaiza | John Snyder | | 564 | 636 | -72 |
| 1999-08-16 | vs ANA | 117 | W 6-1 | 58-59 | 2 | 18,212 | Mike Sirotka | Jarrod Washburn | Mike Sirotka | Jarrod Washburn | | 570 | 637 | -67 |
| 1999-08-17 | vs ANA | 118 | W 4-3 | 59-59 | 2 | 14,943 | Jaime Navarro | Steve Sparks | Bob Howry | Mike Holtz | | 574 | 640 | -66 |
| 1999-08-18 | vs ANA | 119 | W 4-3 | 60-59 | 2 | 11,666 | James Baldwin | Tim Belcher | James Baldwin | Mike Magnante | Bob Howry | 578 | 643 | -65 |
| 1999-08-19 | vs ANA | 120 | L 2-9 | 60-60 | 2 | 14,171 | Jim Parque | Ramon Ortiz | Ramon Ortiz | Jim Parque | | 580 | 652 | -72 |
| 1999-08-21 | @ BAL | 121 | W 4-3 | 61-60 | 3 | 42,901 | John Snyder | Doug Linton | Bill Simas | Alberto Reyes | Bob Howry | 584 | 655 | -71 |
| 1999-08-21 | @ BAL | 122 | W 8-5 | 61-60 | 3 | 47,735 | Mike Sirotka | Sidney Ponson | Bob Howry | Doug Johns | Keith Foulke | 592 | 660 | -68 |
| 1999-08-22 | @ BAL | 123 | L 4-9 | 62-61 | 2 | 43,335 | Jaime Navarro | Mike Mussina | Doug Johns | Jaime Navarro | | 596 | 669 | -73 |
| 1999-08-23 | @ TBA | 124 | W 10-2 | 62-62 | 2 | 15,386 | James Baldwin | Bobby Witt | James Baldwin | Bobby Witt | | 606 | 671 | -65 |
| 1999-08-24 | @ TBA | 125 | L 5-6 | 62-63 | 2 | 15,425 | Jim Parque | Wilson Alvarez | Wilson Alvarez | Jim Parque | Roberto Hernandez | 611 | 677 | -66 |
| 1999-08-25 | @ TBA | 126 | W 6-1 | 63-63 | 2 | 15,468 | Carlos Castillo | Ryan Rupe | Keith Foulke | Ryan Rupe | | 617 | 678 | -61 |
| 1999-08-26 | @ TBA | 127 | L 7-9 | 63-64 | 2 | 16,475 | John Snyder | Dave Eiland | Rick White | John Snyder | Roberto Hernandez | 624 | 687 | -63 |
| 1999-08-27 | vs OAK | 128 | L 6-9 | 63-65 | 2 | 14,270 | Mike Sirotka | Omar Olivares | Omar Olivares | Mike Sirotka | Jason Isringhausen | 630 | 696 | -66 |
| 1999-08-28 | vs OAK | 129 | L 5-7 | 63-66 | 2 | 27,121 | Jaime Navarro | Gil Heredia | Gil Heredia | Jaime Navarro | Doug Jones | 635 | 703 | -68 |
| 1999-08-29 | vs OAK | 130 | W 7-2 | 64-66 | 2 | 16,403 | James Baldwin | Kevin Appier | James Baldwin | Kevin Appier | Keith Foulke | 642 | 705 | -63 |
| 1999-08-30 | vs SEA | 131 | L 2-5 | 64-67 | 3 | 0 | Jim Parque | Freddy Garcia | Freddy Garcia | Jim Parque | Jose Mesa | 644 | 710 | -66 |
| 1999-08-30 | vs SEA | 132 | L 6-14 | 64-67 | 3 | 17,190 | Carlos Castillo | Ken Cloude | Ken Cloude | Carlos Castillo | Frankie Rodriguez | 650 | 724 | -74 |
| 1999-08-31 | vs SEA | 133 | L 4-11 | 66-67 | 2 | 12,579 | John Snyder | John Halama | John Halama | John Snyder | | 654 | 735 | -81 |
| 1999-09-01 | vs SEA | 134 | L 2-3 | 66-68 | 2 | 12,472 | Mike Sirotka | Gil Meche | Gil Meche | Mike Sirotka | Jose Mesa | 656 | 738 | -82 |
| 1999-09-03 | @ TEX | 135 | L 4-10 | 67-68 | 2 | 29,266 | James Baldwin | John Burkett | John Burkett | James Baldwin | | 660 | 748 | -88 |
| 1999-09-04 | @ TEX | 136 | W 12-3 | 67-69 | 2 | 29,279 | Jaime Navarro | Esteban Loaiza | Carlos Castillo | Esteban Loaiza | | 672 | 751 | -79 |
| 1999-09-06 | @ TEX | 137 | L 6-8 | 67-71 | 3 | 0 | Jim Parque | Rick Helling | Rick Helling | Jim Parque | John Wetteland | 678 | 759 | -81 |
| 1999-09-06 | @ TEX | 138 | L 3-6 | 67-71 | 3 | 31,443 | John Snyder | Jeff Fassero | Jeff Fassero | John Snyder | John Wetteland | 681 | 765 | -84 |
| 1999-09-07 | @ ANA | 139 | L 1-14 | 67-72 | 2 | 16,867 | Mike Sirotka | Brian Cooper | Brian Cooper | Mike Sirotka | | 682 | 779 | -97 |
| 1999-09-08 | @ ANA | 140 | L 5-6 | 67-73 | 2 | 17,246 | James Baldwin | Tim Belcher | Troy Percival | Bill Simas | | 687 | 785 | -98 |
| 1999-09-10 | vs CLE | 141 | L 6-14 | 68-73 | 2 | 19,132 | Kip Wells | Bartolo Colon | Bartolo Colon | Kip Wells | | 693 | 799 | -106 |
| 1999-09-11 | vs CLE | 142 | L 3-4 | 68-74 | 2 | 34,400 | Jim Parque | Dave Burba | Dave Burba | Jim Parque | Michael Jackson | 696 | 803 | -107 |
| 1999-09-12 | vs CLE | 143 | W 4-3 | 69-74 | 2 | 20,481 | Mike Sirotka | Jaret Wright | Mike Sirotka | Jaret Wright | Bob Howry | 700 | 806 | -106 |
| 1999-09-13 | vs DET | 144 | L 2-3 | 69-75 | 2 | 12,217 | John Snyder | Dave Mlicki | Dave Mlicki | John Snyder | Todd Jones | 702 | 809 | -107 |
| 1999-09-14 | vs DET | 145 | L 0-7 | 69-76 | 2 | 11,475 | Aaron Myette | C.J. Nitkowski | C.J. Nitkowski | Aaron Myette | | 702 | 816 | -114 |
| 1999-09-15 | vs DET | 146 | W 3-1 | 70-76 | 2 | 11,528 | James Baldwin | Brian Moehler | James Baldwin | Brian Moehler | Keith Foulke | 705 | 817 | -112 |
| 1999-09-17 | @ TOR | 147 | W 7-3 | 71-76 | 2 | 30,743 | Kip Wells | Kelvim Escobar | Kip Wells | Kelvim Escobar | | 712 | 820 | -108 |
| 1999-09-18 | @ TOR | 148 | W 7-4 | 72-76 | 2 | 28,260 | Jim Parque | David Wells | Jaime Navarro | Paul Quantrill | Bob Howry | 719 | 824 | -105 |
| 1999-09-19 | @ TOR | 149 | W 3-2 | 73-76 | 2 | 27,120 | Mike Sirotka | Roy Halladay | Mike Sirotka | Roy Halladay | Bob Howry | 722 | 826 | -104 |
| 1999-09-21 | @ NYA | 150 | L 1-3 | 73-77 | 2 | 29,248 | James Baldwin | Andy Pettitte | Andy Pettitte | James Baldwin | Mariano Rivera | 723 | 829 | -106 |
| 1999-09-22 | @ NYA | 151 | L 4-5 | 73-78 | 2 | 27,549 | Kip Wells | Hideki Irabu | Mariano Rivera | Jaime Navarro | | 727 | 834 | -107 |
| 1999-09-23 | @ NYA | 152 | L 2-5 | 73-79 | 2 | 33,586 | Jim Parque | Roger Clemens | Roger Clemens | Jim Parque | Mariano Rivera | 729 | 839 | -110 |
| 1999-09-24 | @ MIN | 153 | L 2-6 | 73-80 | 2 | 11,308 | Aaron Myette | Joe Mays | Joe Mays | Aaron Myette | | 731 | 845 | -114 |
| 1999-09-25 | @ MIN | 154 | W 13-4 | 73-81 | 2 | 26,324 | Mike Sirotka | LaTroy Hawkins | Mike Sirotka | LaTroy Hawkins | | 744 | 849 | -105 |
| 1999-09-26 | @ MIN | 155 | W 3-0 | 74-81 | 2 | 11,947 | James Baldwin | Jason Ryan | James Baldwin | Jason Ryan | Bob Howry | 747 | 849 | -102 |
| 1999-09-27 | @ MIN | 156 | W 3-1 | 75-81 | 2 | 9,022 | Kip Wells | Brad Radke | Bill Simas | Bob Wells | Keith Foulke | 750 | 850 | -100 |
| 1999-09-29 | vs BOS | 157 | L 2-6 | 75-82 | 3 | 0 | Jim Parque | Kent Mercker | Kent Mercker | Jim Parque | | 752 | 856 | -104 |
| 1999-09-29 | vs BOS | 158 | W 4-2 | 75-82 | 3 | 12,974 | Aaron Myette | Pat Rapp | Keith Foulke | Tom Gordon | Bob Howry | 756 | 858 | -102 |
| 1999-09-30 | vs BOS | 159 | W 5-2 | 77-82 | 2 | 12,788 | Mike Sirotka | Bryce Florie | Sean Lowe | Brian Rose | Bob Howry | 761 | 860 | -99 |
| 1999-10-01 | vs MIN | 160 | W 9-8 | 78-82 | 2 | 11,887 | James Baldwin | Jason Ryan | James Baldwin | Jason Ryan | Bob Howry | 770 | 868 | -98 |
| 1999-10-02 | vs MIN | 161 | W 6-1 | 79-82 | 2 | 17,904 | Kip Wells | Dan Perkins | Kip Wells | Dan Perkins | | 776 | 869 | -93 |
| 1999-10-03 | vs MIN | 162 | W 1-1 | 80-82 | 2 | 18,694 | Tanyon Sturtze | Eric Milton | | | | 777 | 870 | -93 |