| 1999-04-05 | @ TEX | 1 | W 11-5 | 0-1 | 2 | 46,650 | Brian Moehler | Rick Helling | Brian Moehler | Rick Helling | | 11 | 5 | 6 |
| 1999-04-06 | @ TEX | 2 | L 0-6 | 0-2 | 4 | 28,329 | Justin Thompson | Aaron Sele | Aaron Sele | Justin Thompson | | 11 | 11 | 0 |
| 1999-04-07 | @ TEX | 3 | L 7-10 | 1-2 | 4 | 25,004 | Willie Blair | Mark Clark | Mike Morgan | Willie Blair | John Wetteland | 18 | 21 | -3 |
| 1999-04-09 | @ NYA | 4 | L 3-12 | 2-2 | 3 | 56,583 | Beiker Graterol | David Cone | David Cone | Beiker Graterol | | 21 | 33 | -12 |
| 1999-04-10 | @ NYA | 5 | L 0-5 | 2-3 | 4 | 42,058 | Brian Moehler | Roger Clemens | Roger Clemens | Brian Moehler | | 21 | 38 | -17 |
| 1999-04-11 | @ NYA | 6 | L 2-11 | 3-3 | 2 | 32,398 | Justin Thompson | Orlando Hernandez | Orlando Hernandez | Justin Thompson | | 23 | 49 | -26 |
| 1999-04-12 | vs MIN | 7 | L 0-1 | 3-4 | 3 | 47,449 | Willie Blair | Eric Milton | Rick Aguilera | Sean Runyan | | 23 | 50 | -27 |
| 1999-04-14 | vs MIN | 8 | W 7-1 | 4-4 | 2 | 12,263 | Jeff Weaver | LaTroy Hawkins | Jeff Weaver | LaTroy Hawkins | | 30 | 51 | -21 |
| 1999-04-15 | vs MIN | 9 | L 6-8 | 4-5 | 3 | 11,818 | Brian Moehler | Benj Sampson | Bob Wells | Brian Moehler | Rick Aguilera | 36 | 59 | -23 |
| 1999-04-16 | vs NYA | 10 | W 8-1 | 5-5 | 2 | 14,816 | Justin Thompson | Orlando Hernandez | Justin Thompson | Orlando Hernandez | | 44 | 60 | -16 |
| 1999-04-17 | vs NYA | 11 | W 3-1 | 6-5 | 3 | 17,821 | Willie Blair | Andy Pettitte | Matt Anderson | Jeff Nelson | Todd Jones | 47 | 61 | -14 |
| 1999-04-18 | vs NYA | 12 | W 5-1 | 7-5 | 2 | 16,503 | Dave Mlicki | Ramiro Mendoza | Dave Mlicki | Ramiro Mendoza | | 52 | 62 | -10 |
| 1999-04-20 | vs BOS | 13 | L 0-1 | 7-6 | 2 | 12,558 | Jeff Weaver | Pedro Martinez | Pedro Martinez | Jeff Weaver | Derek Lowe | 52 | 63 | -11 |
| 1999-04-21 | vs BOS | 14 | W 9-2 | 8-6 | 2 | 13,049 | Brian Moehler | Tim Wakefield | Brian Moehler | Tim Wakefield | | 61 | 65 | -4 |
| 1999-04-22 | vs BOS | 15 | W 1-0 | 9-6 | 2 | 32,975 | Justin Thompson | Mark Portugal | Justin Thompson | Mark Portugal | Todd Jones | 62 | 65 | -3 |
| 1999-04-23 | @ CHA | 16 | L 0-5 | 9-7 | 3 | 9,837 | Willie Blair | Mike Sirotka | Mike Sirotka | Willie Blair | | 62 | 70 | -8 |
| 1999-04-24 | @ CHA | 17 | L 1-3 | 9-8 | 3 | 11,264 | Dave Mlicki | Jaime Navarro | Jaime Navarro | Dave Mlicki | Bob Howry | 63 | 73 | -10 |
| 1999-04-25 | @ CHA | 18 | W 9-4 | 10-8 | 3 | 15,370 | Jeff Weaver | James Baldwin | Jeff Weaver | James Baldwin | | 72 | 77 | -5 |
| 1999-04-26 | @ SEA | 19 | W 7-0 | 11-8 | 2 | 25,465 | Brian Moehler | Jamie Moyer | Brian Moehler | Jamie Moyer | | 79 | 77 | 2 |
| 1999-04-27 | @ SEA | 20 | W 5-1 | 12-8 | 2 | 19,617 | Justin Thompson | Brett Hinchliffe | Justin Thompson | Brett Hinchliffe | | 84 | 78 | 6 |
| 1999-04-28 | @ SEA | 21 | L 6-8 | 12-9 | 2 | 21,708 | Willie Blair | Freddy Garcia | Freddy Garcia | Willie Blair | | 90 | 86 | 4 |
| 1999-04-29 | @ SEA | 22 | L 6-22 | 13-9 | 2 | 22,078 | Dave Mlicki | Butch Henry | Ken Cloude | C.J. Nitkowski | | 96 | 108 | -12 |
| 1999-04-30 | @ TBA | 23 | W 7-5 | 14-9 | 2 | 19,177 | Jeff Weaver | Rolando Arrojo | Jeff Weaver | Rolando Arrojo | Todd Jones | 103 | 113 | -10 |
| 1999-05-01 | @ TBA | 24 | L 3-4 | 14-10 | 2 | 20,040 | Brian Moehler | Bobby Witt | Bobby Witt | Brian Moehler | Roberto Hernandez | 106 | 117 | -11 |
| 1999-05-02 | @ TBA | 25 | W 8-2 | 15-10 | 2 | 20,644 | Justin Thompson | Julio Santana | Justin Thompson | Julio Santana | | 114 | 119 | -5 |
| 1999-05-03 | @ TBA | 26 | L 6-14 | 16-10 | 1 | 15,430 | Willie Blair | Tony Saunders | Esteban Yan | Willie Blair | | 120 | 133 | -13 |
| 1999-05-04 | vs ANA | 27 | W 3-1 | 17-10 | 1 | 13,411 | Dave Mlicki | Ken Hill | Doug Brocail | Mike Holtz | Todd Jones | 123 | 134 | -11 |
| 1999-05-05 | vs ANA | 28 | L 1-4 | 17-11 | 1 | 12,676 | Jeff Weaver | Steve Sparks | Steve Sparks | Jeff Weaver | Troy Percival | 124 | 138 | -14 |
| 1999-05-06 | vs ANA | 29 | W 4-2 | 18-11 | 1 | 12,510 | Bryce Florie | Chuck Finley | Bryce Florie | Chuck Finley | Todd Jones | 128 | 140 | -12 |
| 1999-05-07 | vs BAL | 30 | L 4-9 | 18-12 | 2 | 15,519 | Justin Thompson | Mike Mussina | Mike Mussina | Justin Thompson | | 132 | 149 | -17 |
| 1999-05-08 | vs BAL | 31 | W 7-6 | 19-12 | 1 | 18,068 | Willie Blair | Scott Kamieniecki | Willie Blair | Scott Kamieniecki | Todd Jones | 139 | 155 | -16 |
| 1999-05-09 | vs BAL | 32 | L 0-5 | 19-13 | 2 | 16,940 | Dave Mlicki | Scott Erickson | Scott Erickson | Dave Mlicki | | 139 | 160 | -21 |
| 1999-05-11 | vs OAK | 33 | L 2-6 | 19-14 | 2 | 12,411 | Jeff Weaver | Kenny Rogers | Brad Rigby | Jeff Weaver | | 141 | 166 | -25 |
| 1999-05-12 | vs OAK | 34 | L 1-2 | 19-15 | 2 | 13,565 | Justin Thompson | Gil Heredia | Gil Heredia | Justin Thompson | Billy Taylor | 142 | 168 | -26 |
| 1999-05-14 | vs CLE | 35 | L 2-4 | 19-16 | 2 | 21,844 | Brian Moehler | Charles Nagy | Steve Karsay | Doug Brocail | Paul Shuey | 144 | 172 | -28 |
| 1999-05-15 | vs CLE | 36 | L 7-12 | 20-16 | 2 | 39,769 | Dave Mlicki | Dave Burba | Dave Burba | Dave Mlicki | | 151 | 184 | -33 |
| 1999-05-16 | vs CLE | 37 | W 9-3 | 21-16 | 2 | 29,731 | Jeff Weaver | Jaret Wright | Jeff Weaver | Jaret Wright | Masao Kida | 160 | 187 | -27 |
| 1999-05-18 | @ TOR | 38 | L 5-7 | 21-17 | 2 | 20,310 | Justin Thompson | Pat Hentgen | Pat Hentgen | Justin Thompson | Billy Koch | 165 | 194 | -29 |
| 1999-05-19 | @ TOR | 39 | W 7-3 | 22-17 | 2 | 20,384 | Brian Moehler | David Wells | Brian Moehler | David Wells | | 172 | 197 | -25 |
| 1999-05-20 | @ TOR | 40 | L 0-7 | 22-18 | 2 | 21,137 | Dave Mlicki | Roy Halladay | Roy Halladay | Dave Mlicki | | 172 | 204 | -32 |
| 1999-05-21 | @ CLE | 41 | W 9-6 | 23-18 | 1 | 43,290 | Willie Blair | Dave Burba | C.J. Nitkowski | Paul Shuey | Todd Jones | 181 | 210 | -29 |
| 1999-05-22 | @ CLE | 42 | W 6-2 | 24-18 | 1 | 40,991 | Jeff Weaver | Jaret Wright | Jeff Weaver | Jaret Wright | | 187 | 212 | -25 |
| 1999-05-23 | @ CLE | 43 | L 4-7 | 24-19 | 1 | 40,874 | Justin Thompson | Bartolo Colon | Paul Shuey | Todd Jones | | 191 | 219 | -28 |
| 1999-05-24 | vs TOR | 44 | L 6-12 | 25-19 | 1 | 13,038 | Brian Moehler | David Wells | David Wells | Brian Moehler | | 197 | 231 | -34 |
| 1999-05-25 | vs TOR | 45 | L 3-5 | 25-20 | 2 | 13,087 | Dave Mlicki | Roy Halladay | Roy Halladay | Dave Mlicki | Billy Koch | 200 | 236 | -36 |
| 1999-05-26 | vs TOR | 46 | L 5-9 | 25-21 | 2 | 14,177 | Willie Blair | Kelvim Escobar | Kelvim Escobar | Willie Blair | Graeme Lloyd | 205 | 245 | -40 |
| 1999-05-27 | vs CHA | 47 | W 10-5 | 25-22 | 2 | 13,465 | Jeff Weaver | John Snyder | Jeff Weaver | John Snyder | | 215 | 250 | -35 |
| 1999-05-28 | vs CHA | 48 | L 1-9 | 25-23 | 2 | 20,437 | Justin Thompson | Jaime Navarro | Jaime Navarro | Justin Thompson | | 216 | 259 | -43 |
| 1999-05-29 | vs CHA | 49 | L 1-7 | 25-24 | 3 | 27,821 | Brian Moehler | James Baldwin | James Baldwin | Brian Moehler | | 217 | 266 | -49 |
| 1999-05-30 | vs CHA | 50 | W 3-2 | 26-24 | 2 | 20,263 | Dave Mlicki | Jim Parque | Dave Mlicki | Jim Parque | Todd Jones | 220 | 268 | -48 |
| 1999-05-31 | @ BOS | 51 | L 7-8 | 26-25 | 3 | 27,883 | Bryce Florie | Mark Portugal | John Wasdin | Matt Anderson | Tom Gordon | 227 | 276 | -49 |
| 1999-06-01 | @ BOS | 52 | L 4-5 | 26-26 | 3 | 26,456 | Jeff Weaver | Bret Saberhagen | John Wasdin | Doug Brocail | Derek Lowe | 231 | 281 | -50 |
| 1999-06-02 | @ BOS | 53 | W 4-2 | 27-26 | 3 | 27,280 | Justin Thompson | Tim Wakefield | Justin Thompson | Tim Wakefield | Todd Jones | 235 | 283 | -48 |
| 1999-06-04 | vs SLN | 54 | W 4-1 | 28-26 | 2 | 40,794 | Brian Moehler | Jose Jimenez | Brian Moehler | Jose Jimenez | Todd Jones | 239 | 284 | -45 |
| 1999-06-05 | vs SLN | 55 | L 2-7 | 28-27 | 2 | 43,679 | Dave Mlicki | Kent Bottenfield | Kent Bottenfield | Willie Blair | Ricky Bottalico | 241 | 291 | -50 |
| 1999-06-06 | vs SLN | 56 | L 4-8 | 28-28 | 3 | 40,898 | Bryce Florie | Juan Acevedo | Rich Croushore | C.J. Nitkowski | Manny Aybar | 245 | 299 | -54 |
| 1999-06-07 | vs PIT | 57 | W 9-4 | 29-28 | 2 | 14,280 | Jeff Weaver | Jason Schmidt | Will Brunson | Jason Schmidt | | 254 | 303 | -49 |
| 1999-06-08 | vs PIT | 58 | W 11-4 | 29-29 | 3 | 15,270 | Nelson Cruz | Todd Ritchie | Nelson Cruz | Todd Ritchie | | 265 | 307 | -42 |
| 1999-06-09 | vs PIT | 59 | L 3-15 | 30-29 | 3 | 15,747 | Brian Moehler | Francisco Cordova | Francisco Cordova | Brian Moehler | | 268 | 322 | -54 |
| 1999-06-11 | @ SLN | 60 | W 8-2 | 31-29 | 3 | 41,927 | Dave Mlicki | Kent Bottenfield | Dave Mlicki | Kent Bottenfield | | 276 | 324 | -48 |
| 1999-06-12 | @ SLN | 61 | L 7-8 | 31-30 | 3 | 47,716 | Jeff Weaver | Juan Acevedo | Scott Radinsky | Willie Blair | | 283 | 332 | -49 |
| 1999-06-13 | @ SLN | 62 | W 3-1 | 32-30 | 3 | 46,269 | Justin Thompson | Lance Painter | Todd Jones | Ricky Bottalico | Doug Brocail | 286 | 333 | -47 |
| 1999-06-14 | vs SEA | 63 | W 8-7 | 33-30 | 3 | 17,291 | Nelson Cruz | Jeff Fassero | Masao Kida | Ken Cloude | | 294 | 340 | -46 |
| 1999-06-15 | vs SEA | 64 | L 4-5 | 33-31 | 3 | 16,659 | Brian Moehler | Frankie Rodriguez | Frankie Rodriguez | Brian Moehler | Jose Mesa | 298 | 345 | -47 |
| 1999-06-16 | vs SEA | 65 | L 1-7 | 33-32 | 3 | 17,136 | Dave Mlicki | Jamie Moyer | Jamie Moyer | Dave Mlicki | | 299 | 352 | -53 |
| 1999-06-17 | vs SEA | 66 | L 3-4 | 33-33 | 3 | 18,415 | Jeff Weaver | Freddy Garcia | Freddy Garcia | Todd Jones | Jose Mesa | 302 | 356 | -54 |
| 1999-06-18 | vs OAK | 67 | W 8-3 | 34-33 | 3 | 22,347 | Justin Thompson | Mike Oquist | Justin Thompson | Mike Oquist | | 310 | 359 | -49 |
| 1999-06-19 | vs OAK | 68 | L 1-13 | 34-34 | 3 | 24,704 | Nelson Cruz | Tim Hudson | Tim Hudson | Nelson Cruz | | 311 | 372 | -61 |
| 1999-06-20 | vs OAK | 69 | L 5-6 | 34-35 | 3 | 25,934 | Brian Moehler | Jimmy Haynes | Jimmy Haynes | Brian Moehler | Billy Taylor | 316 | 378 | -62 |
| 1999-06-21 | vs OAK | 70 | W 13-11 | 35-35 | 3 | 16,083 | Dave Mlicki | Gil Heredia | Doug Brocail | Brad Rigby | Todd Jones | 329 | 389 | -60 |
| 1999-06-22 | @ KCA | 71 | L 2-4 | 35-36 | 3 | 14,696 | Jeff Weaver | Jose Rosado | Jose Rosado | Bryce Florie | Scott Service | 331 | 393 | -62 |
| 1999-06-23 | @ KCA | 72 | L 1-10 | 35-37 | 3 | 19,021 | Justin Thompson | Jay Witasick | Jay Witasick | Justin Thompson | | 332 | 403 | -71 |
| 1999-06-24 | @ KCA | 73 | W 6-4 | 36-37 | 3 | 22,506 | Nelson Cruz | Kevin Appier | Nelson Cruz | Terry Mathews | Todd Jones | 338 | 407 | -69 |
| 1999-06-25 | vs MIN | 74 | W 2-0 | 37-37 | 3 | 21,604 | Brian Moehler | Eric Milton | Brian Moehler | Eric Milton | | 340 | 407 | -67 |
| 1999-06-26 | vs MIN | 75 | L 0-1 | 37-38 | 3 | 19,667 | Dave Mlicki | Joe Mays | Joe Mays | Dave Mlicki | Mike Trombley | 340 | 408 | -68 |
| 1999-06-27 | vs MIN | 76 | L 7-12 | 38-38 | 3 | 21,355 | Jeff Weaver | LaTroy Hawkins | LaTroy Hawkins | Jeff Weaver | | 347 | 420 | -73 |
| 1999-06-29 | @ NYA | 77 | L 0-3 | 38-39 | 3 | 31,338 | Justin Thompson | Roger Clemens | Roger Clemens | Justin Thompson | | 347 | 423 | -76 |
| 1999-06-30 | @ NYA | 78 | W 8-2 | 39-39 | 3 | 39,749 | Brian Moehler | Andy Pettitte | Brian Moehler | Andy Pettitte | | 355 | 425 | -70 |
| 1999-07-01 | @ NYA | 79 | L 0-6 | 39-40 | 3 | 26,311 | Dave Mlicki | Hideki Irabu | Hideki Irabu | Dave Mlicki | | 355 | 431 | -76 |
| 1999-07-02 | @ MIN | 80 | L 4-11 | 40-40 | 3 | 12,033 | Jeff Weaver | LaTroy Hawkins | LaTroy Hawkins | Jeff Weaver | | 359 | 442 | -83 |
| 1999-07-03 | @ MIN | 81 | L 2-7 | 40-41 | 4 | 14,042 | Nelson Cruz | Mike Lincoln | Mike Lincoln | Nelson Cruz | | 361 | 449 | -88 |
| 1999-07-04 | @ MIN | 82 | W 15-5 | 40-42 | 3 | 13,094 | Justin Thompson | Dan Perkins | Justin Thompson | Dan Perkins | | 376 | 454 | -78 |
| 1999-07-06 | vs NYA | 83 | L 8-9 | 40-43 | 3 | 23,785 | Brian Moehler | Hideki Irabu | Mariano Rivera | Todd Jones | Ramiro Mendoza | 384 | 463 | -79 |
| 1999-07-07 | vs NYA | 84 | W 6-4 | 41-43 | 3 | 28,844 | Dave Mlicki | David Cone | Dave Mlicki | David Cone | Doug Brocail | 390 | 467 | -77 |
| 1999-07-08 | vs NYA | 85 | L 2-3 | 41-44 | 3 | 34,417 | Jeff Weaver | Orlando Hernandez | Orlando Hernandez | C.J. Nitkowski | Mariano Rivera | 392 | 470 | -78 |
| 1999-07-09 | vs MIL | 86 | L 1-4 | 41-45 | 3 | 22,769 | Nelson Cruz | Steve Woodard | Steve Woodard | Nelson Cruz | Bob Wickman | 393 | 474 | -81 |
| 1999-07-10 | vs MIL | 87 | W 9-3 | 42-45 | 3 | 25,374 | Justin Thompson | Jim Abbott | Justin Thompson | Jim Abbott | | 402 | 477 | -75 |
| 1999-07-11 | vs MIL | 88 | L 2-3 | 42-46 | 3 | 32,974 | Brian Moehler | Hideo Nomo | Hideo Nomo | Brian Moehler | Bob Wickman | 404 | 480 | -76 |
| 1999-07-15 | @ HOU | 89 | L 6-8 | 42-47 | 3 | 32,573 | Dave Mlicki | Shane Reynolds | Trever Miller | Willie Blair | Billy Wagner | 410 | 488 | -78 |
| 1999-07-16 | @ HOU | 90 | L 1-2 | 42-48 | 3 | 36,541 | Justin Thompson | Scott Elarton | Jose Cabrera | Doug Brocail | | 411 | 490 | -79 |
| 1999-07-17 | @ HOU | 91 | L 2-3 | 42-49 | 3 | 41,177 | Dave Borkowski | Jose Lima | Billy Wagner | Todd Jones | | 413 | 493 | -80 |
| 1999-07-18 | @ CIN | 92 | W 9-8 | 43-49 | 3 | 26,657 | Brian Moehler | Steve Avery | Doug Brocail | Danny Graves | Todd Jones | 422 | 501 | -79 |
| 1999-07-19 | @ CIN | 93 | W 7-6 | 44-49 | 3 | 20,291 | Jeff Weaver | Pete Harnisch | C.J. Nitkowski | Scott Sullivan | Todd Jones | 429 | 507 | -78 |
| 1999-07-20 | @ CIN | 94 | L 2-5 | 44-50 | 3 | 17,888 | Dave Mlicki | Steve Parris | Steve Parris | Dave Mlicki | Danny Graves | 431 | 512 | -81 |
| 1999-07-21 | vs KCA | 95 | W 10-5 | 44-51 | 3 | 19,064 | Justin Thompson | Kevin Appier | Justin Thompson | Kevin Appier | | 441 | 517 | -76 |
| 1999-07-22 | vs KCA | 96 | W 9-8 | 45-51 | 3 | 29,322 | Dave Borkowski | Jose Rosado | Bryce Florie | Jose Rosado | Todd Jones | 450 | 525 | -75 |
| 1999-07-23 | vs BOS | 97 | W 14-5 | 45-52 | 3 | 35,245 | Brian Moehler | Tomo Ohka | Brian Moehler | Tomo Ohka | | 464 | 530 | -66 |
| 1999-07-24 | vs BOS | 98 | L 4-11 | 46-52 | 3 | 37,149 | Jeff Weaver | Mark Portugal | Mark Portugal | Jeff Weaver | Derek Lowe | 468 | 541 | -73 |
| 1999-07-25 | vs BOS | 99 | W 9-1 | 47-52 | 3 | 34,959 | Dave Mlicki | Brian Rose | Dave Mlicki | Brian Rose | | 477 | 542 | -65 |
| 1999-07-26 | @ CLE | 100 | L 3-6 | 47-53 | 3 | 43,157 | Justin Thompson | Dave Burba | Dave Burba | Justin Thompson | Michael Jackson | 480 | 548 | -68 |
| 1999-07-27 | @ CLE | 101 | L 5-14 | 48-53 | 3 | 43,042 | Dave Borkowski | Charles Nagy | Charles Nagy | Dave Borkowski | | 485 | 562 | -77 |
| 1999-07-28 | @ CLE | 102 | L 2-7 | 48-54 | 3 | 43,162 | Brian Moehler | Dwight Gooden | Dwight Gooden | Brian Moehler | | 487 | 569 | -82 |
| 1999-07-30 | @ TOR | 103 | L 2-8 | 48-55 | 3 | 28,412 | Jeff Weaver | Kelvim Escobar | Kelvim Escobar | Jeff Weaver | | 489 | 577 | -88 |
| 1999-07-31 | @ TOR | 104 | L 6-7 | 48-56 | 3 | 29,527 | Dave Mlicki | Chris Carpenter | Roy Halladay | Dave Mlicki | Billy Koch | 495 | 584 | -89 |
| 1999-08-01 | @ TOR | 105 | L 5-8 | 48-57 | 3 | 30,105 | Dave Borkowski | Pat Hentgen | Pat Hentgen | Dave Borkowski | Billy Koch | 500 | 592 | -92 |
| 1999-08-02 | vs CHA | 106 | L 2-6 | 48-58 | 3 | 26,637 | Brian Moehler | Kip Wells | Kip Wells | Brian Moehler | | 502 | 598 | -96 |
| 1999-08-03 | vs CHA | 107 | L 6-9 | 48-59 | 3 | 24,484 | Justin Thompson | John Snyder | John Snyder | Justin Thompson | Bob Howry | 508 | 607 | -99 |
| 1999-08-05 | @ BAL | 108 | L 3-6 | 48-60 | 3 | 40,886 | Jeff Weaver | Sidney Ponson | Sidney Ponson | Jeff Weaver | Mike Timlin | 511 | 613 | -102 |
| 1999-08-06 | @ BAL | 109 | W 4-3 | 49-60 | 3 | 41,708 | Dave Mlicki | Mike Mussina | Dave Mlicki | Mike Mussina | Todd Jones | 515 | 616 | -101 |
| 1999-08-07 | @ BAL | 110 | L 4-5 | 49-61 | 3 | 48,505 | Dave Borkowski | Scott Erickson | Scott Erickson | Dave Borkowski | Mike Timlin | 519 | 621 | -102 |
| 1999-08-08 | @ BAL | 111 | W 5-2 | 50-61 | 3 | 44,474 | Brian Moehler | Ricky Bones | Doug Brocail | Scott Kamieniecki | Todd Jones | 524 | 623 | -99 |
| 1999-08-10 | @ TEX | 112 | L 3-4 | 50-62 | 3 | 24,398 | Justin Thompson | Esteban Loaiza | Danny Patterson | Nelson Cruz | | 527 | 627 | -100 |
| 1999-08-11 | @ TEX | 113 | L 2-8 | 50-63 | 3 | 27,432 | Willie Blair | Rick Helling | Rick Helling | Willie Blair | | 529 | 635 | -106 |
| 1999-08-12 | @ TEX | 114 | W 3-1 | 51-63 | 3 | 27,209 | Dave Mlicki | Aaron Sele | Dave Mlicki | Aaron Sele | Todd Jones | 532 | 636 | -104 |
| 1999-08-13 | vs ANA | 115 | W 8-7 | 52-63 | 4 | 32,003 | Dave Borkowski | Tim Belcher | Todd Jones | Shigetoshi Hasegawa | | 540 | 643 | -103 |
| 1999-08-14 | vs ANA | 116 | L 4-7 | 52-64 | 4 | 36,651 | Brian Moehler | Ken Hill | Mike Magnante | Brian Moehler | Troy Percival | 544 | 650 | -106 |
| 1999-08-15 | vs ANA | 117 | L 2-10 | 53-64 | 4 | 34,237 | Justin Thompson | Chuck Finley | Chuck Finley | Justin Thompson | | 546 | 660 | -114 |
| 1999-08-16 | vs TBA | 118 | L 1-9 | 53-65 | 4 | 21,102 | Jeff Weaver | Rolando Arrojo | Rolando Arrojo | Jeff Weaver | | 547 | 669 | -122 |
| 1999-08-17 | vs TBA | 119 | W 3-1 | 54-65 | 3 | 19,418 | Dave Mlicki | Bobby Witt | Dave Mlicki | Bobby Witt | Todd Jones | 550 | 670 | -120 |
| 1999-08-18 | vs TBA | 120 | L 0-4 | 54-66 | 3 | 21,311 | Dave Borkowski | Wilson Alvarez | Wilson Alvarez | Dave Borkowski | Albie Lopez | 550 | 674 | -124 |
| 1999-08-20 | @ ANA | 121 | L 1-5 | 54-67 | 3 | 29,910 | Brian Moehler | Chuck Finley | Chuck Finley | Brian Moehler | | 551 | 679 | -128 |
| 1999-08-21 | @ ANA | 122 | W 5-0 | 55-67 | 4 | 28,575 | Jeff Weaver | Jarrod Washburn | Jeff Weaver | Jarrod Washburn | | 556 | 679 | -123 |
| 1999-08-22 | @ ANA | 123 | W 12-3 | 55-68 | 3 | 24,465 | Dave Mlicki | Steve Sparks | Dave Mlicki | Steve Sparks | | 568 | 682 | -114 |
| 1999-08-23 | @ ANA | 124 | L 5-6 | 55-69 | 3 | 17,145 | Dave Borkowski | Tim Belcher | Troy Percival | Doug Brocail | | 573 | 688 | -115 |
| 1999-08-24 | @ SEA | 125 | L 0-5 | 55-70 | 3 | 42,517 | Willie Blair | Freddy Garcia | Freddy Garcia | Willie Blair | | 573 | 693 | -120 |
| 1999-08-25 | @ SEA | 126 | L 2-3 | 55-71 | 4 | 43,789 | Brian Moehler | John Halama | John Halama | Brian Moehler | Jose Mesa | 575 | 696 | -121 |
| 1999-08-27 | vs BAL | 127 | W 5-4 | 56-71 | 4 | 37,600 | Jeff Weaver | Doug Johns | Jeff Weaver | Alberto Reyes | Todd Jones | 580 | 700 | -120 |
| 1999-08-28 | vs BAL | 128 | W 4-3 | 57-71 | 4 | 42,377 | Dave Mlicki | Scott Erickson | Dave Mlicki | Scott Erickson | Todd Jones | 584 | 703 | -119 |
| 1999-08-29 | vs BAL | 129 | L 4-11 | 58-71 | 4 | 37,911 | C.J. Nitkowski | Jason Johnson | Jason Johnson | C.J. Nitkowski | | 588 | 714 | -126 |
| 1999-08-30 | vs TEX | 130 | W 1-0 | 59-71 | 4 | 19,007 | Brian Moehler | Esteban Loaiza | Brian Moehler | Esteban Loaiza | | 589 | 714 | -125 |
| 1999-08-31 | vs TEX | 131 | W 14-6 | 59-72 | 3 | 17,439 | Dave Borkowski | Mike Morgan | Francisco Cordero | Danny Kolb | | 603 | 720 | -117 |
| 1999-09-01 | vs TEX | 132 | L 7-14 | 60-72 | 3 | 18,544 | Jeff Weaver | Rick Helling | Rick Helling | Jeff Weaver | John Wetteland | 610 | 734 | -124 |
| 1999-09-02 | vs TEX | 133 | W 8-7 | 61-72 | 3 | 22,945 | Dave Mlicki | Aaron Sele | Dave Mlicki | Jeff Zimmerman | Todd Jones | 618 | 741 | -123 |
| 1999-09-03 | @ OAK | 134 | L 4-7 | 61-73 | 3 | 10,297 | C.J. Nitkowski | Kevin Appier | Kevin Appier | Nelson Cruz | Jason Isringhausen | 622 | 748 | -126 |
| 1999-09-04 | @ OAK | 135 | L 1-2 | 61-74 | 3 | 18,323 | Brian Moehler | Tim Hudson | Tim Hudson | Francisco Cordero | | 623 | 750 | -127 |
| 1999-09-05 | @ OAK | 136 | W 5-4 | 62-74 | 3 | 20,429 | Willie Blair | Jimmy Haynes | Willie Blair | Jimmy Haynes | Todd Jones | 628 | 754 | -126 |
| 1999-09-06 | @ OAK | 137 | W 9-7 | 63-74 | 4 | 30,541 | Jeff Weaver | Omar Olivares | Dave Borkowski | Omar Olivares | Todd Jones | 637 | 761 | -124 |
| 1999-09-08 | @ TBA | 138 | W 5-1 | 64-74 | 3 | 14,887 | Dave Mlicki | Bobby Witt | Dave Mlicki | Bobby Witt | | 642 | 762 | -120 |
| 1999-09-09 | @ TBA | 139 | L 3-5 | 64-75 | 3 | 15,056 | C.J. Nitkowski | Rolando Arrojo | Rolando Arrojo | C.J. Nitkowski | Roberto Hernandez | 645 | 767 | -122 |
| 1999-09-10 | vs TOR | 140 | W 7-6 | 65-75 | 3 | 33,736 | Brian Moehler | Pat Hentgen | Todd Jones | John Frascatore | | 652 | 773 | -121 |
| 1999-09-11 | vs TOR | 141 | L 5-9 | 65-76 | 3 | 40,269 | Willie Blair | Chris Carpenter | Paul Spoljaric | Francisco Cordero | | 657 | 782 | -125 |
| 1999-09-12 | vs TOR | 142 | L 3-5 | 65-77 | 3 | 39,349 | Jeff Weaver | Kelvim Escobar | Kelvim Escobar | Jeff Weaver | Billy Koch | 660 | 787 | -127 |
| 1999-09-13 | @ CHA | 143 | W 3-2 | 66-77 | 3 | 12,217 | Dave Mlicki | John Snyder | Dave Mlicki | John Snyder | Todd Jones | 663 | 789 | -126 |
| 1999-09-14 | @ CHA | 144 | W 7-0 | 67-77 | 3 | 11,475 | C.J. Nitkowski | Aaron Myette | C.J. Nitkowski | Aaron Myette | | 670 | 789 | -119 |
| 1999-09-15 | @ CHA | 145 | L 1-3 | 67-78 | 3 | 11,528 | Brian Moehler | James Baldwin | James Baldwin | Brian Moehler | Keith Foulke | 671 | 792 | -121 |
| 1999-09-17 | @ BOS | 146 | L 3-14 | 68-78 | 3 | 29,038 | Willie Blair | Pat Rapp | Bryce Florie | Willie Blair | | 674 | 806 | -132 |
| 1999-09-18 | @ BOS | 147 | L 1-9 | 68-79 | 3 | 32,382 | Jeff Weaver | Bret Saberhagen | Bret Saberhagen | Jeff Weaver | | 675 | 815 | -140 |
| 1999-09-19 | @ BOS | 148 | L 3-7 | 68-80 | 3 | 30,777 | Dave Mlicki | Tim Wakefield | Tim Wakefield | Dave Mlicki | Derek Lowe | 678 | 822 | -144 |
| 1999-09-20 | vs CLE | 149 | W 4-3 | 69-80 | 3 | 26,106 | C.J. Nitkowski | Dwight Gooden | Todd Jones | David Riske | | 682 | 825 | -143 |
| 1999-09-21 | vs CLE | 150 | L 1-6 | 69-81 | 3 | 24,155 | Dave Borkowski | Dave Burba | Dave Burba | Dave Borkowski | | 683 | 831 | -148 |
| 1999-09-22 | vs CLE | 151 | L 1-9 | 69-82 | 3 | 27,355 | Brian Moehler | Jaret Wright | Jaret Wright | Brian Moehler | | 684 | 840 | -156 |
| 1999-09-23 | vs CLE | 152 | W 7-5 | 70-82 | 3 | 34,970 | Willie Blair | Charles Nagy | Willie Blair | Charles Nagy | Todd Jones | 691 | 845 | -154 |
| 1999-09-24 | vs KCA | 153 | L 3-7 | 70-83 | 3 | 39,030 | Dave Mlicki | Jose Rosado | Jose Rosado | Dave Mlicki | | 694 | 852 | -158 |
| 1999-09-25 | vs KCA | 154 | W 11-3 | 70-84 | 3 | 41,164 | C.J. Nitkowski | Mac Suzuki | C.J. Nitkowski | Mac Suzuki | | 705 | 855 | -150 |
| 1999-09-26 | vs KCA | 155 | W 6-1 | 71-84 | 3 | 41,586 | Dave Borkowski | Blake Stein | Dave Borkowski | Blake Stein | | 711 | 856 | -145 |
| 1999-09-27 | vs KCA | 156 | W 8-2 | 72-84 | 3 | 43,356 | Brian Moehler | Jeff Suppan | Brian Moehler | Jeff Suppan | | 719 | 858 | -139 |
| 1999-09-28 | @ MIN | 157 | W 7-4 | 73-84 | 3 | 11,875 | Willie Blair | Eric Milton | Matt Anderson | Mike Trombley | Todd Jones | 726 | 862 | -136 |
| 1999-09-29 | @ MIN | 158 | W 6-3 | 74-84 | 4 | 9,933 | Dave Mlicki | Joe Mays | Dave Mlicki | Joe Mays | Todd Jones | 732 | 865 | -133 |
| 1999-09-30 | @ MIN | 159 | W 6-5 | 75-84 | 3 | 11,464 | C.J. Nitkowski | LaTroy Hawkins | Francisco Cordero | Bob Wells | Todd Jones | 738 | 870 | -132 |
| 1999-10-01 | @ KCA | 160 | L 5-9 | 75-85 | 3 | 13,382 | Dave Borkowski | Blake Stein | Mac Suzuki | Dave Borkowski | | 743 | 879 | -136 |
| 1999-10-02 | @ KCA | 161 | W 4-3 | 76-85 | 3 | 17,204 | Jeff Weaver | Jeff Suppan | Jeff Weaver | Jeff Suppan | Todd Jones | 747 | 882 | -135 |