| 1999-04-05 | @ BAL | 1 | L 7-10 | 1-0 | 2 | 46,733 | Wilson Alvarez | Mike Mussina | Mike Mussina | Wilson Alvarez | Mike Timlin | 7 | 10 | -3 |
| 1999-04-07 | @ BAL | 2 | W 8-5 | 2-0 | 2 | 42,284 | Tony Saunders | Juan Guzman | Tony Saunders | Juan Guzman | Roberto Hernandez | 15 | 15 | 0 |
| 1999-04-08 | @ BAL | 3 | W 6-3 | 3-0 | 2 | 39,853 | Bobby Witt | Scott Erickson | Bobby Witt | Scott Erickson | | 21 | 18 | 3 |
| 1999-04-09 | vs BOS | 4 | L 1-4 | 3-1 | 2 | 40,525 | Rolando Arrojo | Mark Portugal | Mark Portugal | Rolando Arrojo | | 22 | 22 | 0 |
| 1999-04-10 | vs BOS | 5 | L 3-5 | 3-2 | 3 | 28,522 | Julio Santana | Pedro Martinez | Pedro Martinez | Julio Santana | Tom Gordon | 25 | 27 | -2 |
| 1999-04-11 | vs BOS | 6 | W 5-4 | 4-2 | 2 | 23,404 | Wilson Alvarez | Pat Rapp | Scott Aldred | Derek Lowe | Roberto Hernandez | 30 | 31 | -1 |
| 1999-04-12 | @ TOR | 7 | L 1-7 | 4-3 | 3 | 37,160 | Tony Saunders | David Wells | David Wells | Tony Saunders | | 31 | 38 | -7 |
| 1999-04-13 | @ TOR | 8 | W 8-5 | 5-3 | 2 | 23,710 | Bobby Witt | Joey Hamilton | Rick White | Joey Hamilton | Roberto Hernandez | 39 | 43 | -4 |
| 1999-04-14 | @ TOR | 9 | L 6-7 | 5-4 | 3 | 23,847 | Rolando Arrojo | Kelvim Escobar | Graeme Lloyd | Albie Lopez | | 45 | 50 | -5 |
| 1999-04-15 | @ TOR | 10 | L 1-11 | 5-5 | 3 | 23,765 | Julio Santana | Chris Carpenter | Chris Carpenter | Julio Santana | | 46 | 61 | -15 |
| 1999-04-16 | @ BOS | 11 | W 6-2 | 6-5 | 3 | 18,809 | Bryan Rekar | Tim Wakefield | Bryan Rekar | Tim Wakefield | | 52 | 63 | -11 |
| 1999-04-17 | @ BOS | 12 | L 5-8 | 6-6 | 3 | 26,799 | Tony Saunders | Mark Portugal | Mark Portugal | Tony Saunders | | 57 | 71 | -14 |
| 1999-04-18 | @ BOS | 13 | W 5-1 | 7-6 | 3 | 27,589 | Bobby Witt | Pat Rapp | Bobby Witt | Pat Rapp | | 62 | 72 | -10 |
| 1999-04-19 | @ BOS | 14 | W 4-1 | 8-6 | 3 | 33,167 | Rolando Arrojo | Bret Saberhagen | Rolando Arrojo | Bret Saberhagen | Roberto Hernandez | 66 | 73 | -7 |
| 1999-04-20 | vs BAL | 15 | W 5-3 | 9-6 | 3 | 17,660 | Julio Santana | Scott Erickson | Julio Santana | Scott Erickson | Roberto Hernandez | 71 | 76 | -5 |
| 1999-04-21 | vs BAL | 16 | W 14-8 | 9-7 | 3 | 22,119 | Bryan Rekar | Mike Mussina | Bryan Rekar | Mike Mussina | | 85 | 84 | 1 |
| 1999-04-22 | vs BAL | 17 | W 1-0 | 10-7 | 2 | 17,334 | Tony Saunders | Sidney Ponson | Tony Saunders | Sidney Ponson | Roberto Hernandez | 86 | 84 | 2 |
| 1999-04-23 | vs SEA | 18 | W 5-4 | 11-7 | 2 | 20,322 | Bobby Witt | Freddy Garcia | Rick White | John Halama | Roberto Hernandez | 91 | 88 | 3 |
| 1999-04-24 | vs SEA | 19 | L 4-9 | 11-8 | 2 | 26,065 | Rolando Arrojo | Butch Henry | Butch Henry | Rolando Arrojo | | 95 | 97 | -2 |
| 1999-04-25 | vs SEA | 20 | L 4-6 | 11-9 | 3 | 27,163 | Julio Santana | Jeff Fassero | Jose Paniagua | Roberto Hernandez | Jose Mesa | 99 | 103 | -4 |
| 1999-04-28 | @ CHA | 21 | L 7-10 | 12-10 | 3 | 0 | Bryan Rekar | Jim Parque | Jim Parque | Bryan Rekar | Bob Howry | 106 | 113 | -7 |
| 1999-04-28 | @ CHA | 22 | L 1-9 | 12-10 | 3 | 10,300 | Tony Saunders | John Snyder | John Snyder | Tony Saunders | | 107 | 122 | -15 |
| 1999-04-29 | @ CHA | 23 | W 4-1 | 13-10 | 2 | 10,022 | Wilson Alvarez | Mike Sirotka | Wilson Alvarez | Mike Sirotka | Roberto Hernandez | 111 | 123 | -12 |
| 1999-04-30 | vs DET | 24 | L 5-7 | 13-11 | 4 | 19,177 | Rolando Arrojo | Jeff Weaver | Jeff Weaver | Rolando Arrojo | Todd Jones | 116 | 130 | -14 |
| 1999-05-01 | vs DET | 25 | W 4-3 | 14-11 | 4 | 20,040 | Bobby Witt | Brian Moehler | Bobby Witt | Brian Moehler | Roberto Hernandez | 120 | 133 | -13 |
| 1999-05-02 | vs DET | 26 | L 2-8 | 14-12 | 4 | 20,644 | Julio Santana | Justin Thompson | Justin Thompson | Julio Santana | | 122 | 141 | -19 |
| 1999-05-03 | vs DET | 27 | W 14-6 | 14-13 | 4 | 15,430 | Tony Saunders | Willie Blair | Esteban Yan | Willie Blair | | 136 | 147 | -11 |
| 1999-05-04 | vs KCA | 28 | L 3-5 | 14-14 | 4 | 15,470 | Wilson Alvarez | Jeff Suppan | Terry Mathews | Roberto Hernandez | Jeff Montgomery | 139 | 152 | -13 |
| 1999-05-05 | vs KCA | 29 | W 10-7 | 14-15 | 4 | 16,111 | Ryan Rupe | Jay Witasick | Rick White | Jay Witasick | Roberto Hernandez | 149 | 159 | -10 |
| 1999-05-06 | vs KCA | 30 | W 5-4 | 15-15 | 4 | 15,321 | Rolando Arrojo | Jim Pittsley | Scott Aldred | Alvin Morman | Roberto Hernandez | 154 | 163 | -9 |
| 1999-05-07 | @ CLE | 31 | L 11-20 | 15-16 | 4 | 40,601 | Bobby Witt | Dwight Gooden | Paul Wagner | Jim Mecir | | 165 | 183 | -18 |
| 1999-05-08 | @ CLE | 32 | W 7-6 | 16-16 | 4 | 40,590 | Esteban Yan | Charles Nagy | Bryan Rekar | Charles Nagy | Roberto Hernandez | 172 | 189 | -17 |
| 1999-05-09 | @ CLE | 33 | L 4-5 | 16-17 | 4 | 42,835 | Wilson Alvarez | Jaret Wright | Jaret Wright | Wilson Alvarez | Michael Jackson | 176 | 194 | -18 |
| 1999-05-11 | vs MIN | 34 | L 1-2 | 16-18 | 4 | 17,227 | Ryan Rupe | Brad Radke | Brad Radke | Ryan Rupe | Rick Aguilera | 177 | 196 | -19 |
| 1999-05-12 | vs MIN | 35 | L 4-9 | 16-19 | 4 | 18,068 | Rolando Arrojo | Eric Milton | Eric Milton | Rolando Arrojo | Mike Trombley | 181 | 205 | -24 |
| 1999-05-14 | @ ANA | 36 | L 3-8 | 16-20 | 5 | 35,515 | Bobby Witt | Tim Belcher | Tim Belcher | Bobby Witt | | 184 | 213 | -29 |
| 1999-05-15 | @ ANA | 37 | W 3-1 | 17-20 | 4 | 36,939 | Tony Saunders | Ken Hill | Tony Saunders | Ken Hill | Roberto Hernandez | 187 | 214 | -27 |
| 1999-05-16 | @ ANA | 38 | W 7-4 | 18-20 | 4 | 35,064 | Wilson Alvarez | Steve Sparks | Wilson Alvarez | Steve Sparks | | 194 | 218 | -24 |
| 1999-05-17 | @ TEX | 39 | W 13-3 | 18-21 | 4 | 29,946 | Ryan Rupe | John Burkett | Ryan Rupe | John Burkett | | 207 | 221 | -14 |
| 1999-05-18 | @ TEX | 40 | W 5-4 | 19-21 | 4 | 29,706 | Rolando Arrojo | Mike Morgan | Rolando Arrojo | Mike Morgan | Roberto Hernandez | 212 | 225 | -13 |
| 1999-05-19 | @ TEX | 41 | L 6-7 | 19-22 | 4 | 29,513 | Bobby Witt | Mark Clark | Jeff Zimmerman | Scott Aldred | John Wetteland | 218 | 232 | -14 |
| 1999-05-21 | vs ANA | 42 | W 10-9 | 19-23 | 4 | 20,687 | Tony Saunders | Ken Hill | Rick White | Mike Magnante | Roberto Hernandez | 228 | 241 | -13 |
| 1999-05-22 | vs ANA | 43 | L 6-8 | 19-24 | 5 | 23,168 | Wilson Alvarez | Steve Sparks | Mark Petkovsek | Alan Newman | Troy Percival | 234 | 249 | -15 |
| 1999-05-23 | vs ANA | 44 | L 0-4 | 19-25 | 4 | 22,522 | Ryan Rupe | Chuck Finley | Chuck Finley | Roberto Hernandez | | 234 | 253 | -19 |
| 1999-05-24 | vs TEX | 45 | L 3-12 | 20-25 | 4 | 15,820 | Rolando Arrojo | Mark Clark | Mark Clark | Rolando Arrojo | | 237 | 265 | -28 |
| 1999-05-25 | vs TEX | 46 | L 2-7 | 20-26 | 4 | 16,058 | Bobby Witt | Ryan Glynn | Mike Venafro | Bobby Witt | | 239 | 272 | -33 |
| 1999-05-26 | vs TEX | 47 | L 6-8 | 20-27 | 4 | 17,575 | Tony Saunders | Rick Helling | Rick Helling | Julio Santana | John Wetteland | 245 | 280 | -35 |
| 1999-05-28 | @ SEA | 48 | L 1-6 | 20-28 | 5 | 25,421 | Wilson Alvarez | Freddy Garcia | Freddy Garcia | Wilson Alvarez | | 246 | 286 | -40 |
| 1999-05-29 | @ SEA | 49 | L 5-11 | 21-28 | 5 | 38,093 | Ryan Rupe | Jeff Fassero | Jeff Fassero | Ryan Rupe | | 251 | 297 | -46 |
| 1999-05-30 | @ SEA | 50 | W 15-7 | 21-29 | 5 | 28,090 | Bryan Rekar | Ken Cloude | Bryan Rekar | Ken Cloude | | 266 | 304 | -38 |
| 1999-05-31 | @ OAK | 51 | L 7-10 | 22-29 | 5 | 10,444 | Bobby Witt | Jimmy Haynes | Buddy Groom | Esteban Yan | | 273 | 314 | -41 |
| 1999-06-01 | @ OAK | 52 | L 2-5 | 22-30 | 5 | 7,170 | Dave Eiland | Kenny Rogers | Kenny Rogers | Dave Eiland | Billy Taylor | 275 | 319 | -44 |
| 1999-06-02 | @ OAK | 53 | W 7-6 | 23-30 | 5 | 17,505 | Wilson Alvarez | Tom Candiotti | Esteban Yan | T.J. Mathews | Roberto Hernandez | 282 | 325 | -43 |
| 1999-06-04 | vs FLO | 54 | L 0-10 | 23-31 | 5 | 20,167 | Ryan Rupe | Dennis Springer | Dennis Springer | Ryan Rupe | | 282 | 335 | -53 |
| 1999-06-05 | vs FLO | 55 | L 7-9 | 23-32 | 5 | 22,686 | Bryan Rekar | Brian Meadows | Brian Meadows | Mike Duvall | Matt Mantei | 289 | 344 | -55 |
| 1999-06-06 | vs FLO | 56 | L 6-11 | 24-32 | 5 | 21,321 | Bobby Witt | Livan Hernandez | Antonio Alfonseca | Esteban Yan | | 295 | 355 | -60 |
| 1999-06-07 | @ ATL | 57 | L 5-9 | 24-33 | 5 | 36,731 | Dave Eiland | John Smoltz | John Smoltz | Dave Eiland | John Rocker | 300 | 364 | -64 |
| 1999-06-08 | @ ATL | 58 | L 2-11 | 25-33 | 6 | 35,709 | Wilson Alvarez | Odalis Perez | Odalis Perez | Wilson Alvarez | | 302 | 375 | -73 |
| 1999-06-09 | @ ATL | 59 | L 3-4 | 25-34 | 5 | 35,160 | Ryan Rupe | Tom Glavine | Kevin McGlinchy | Rick White | | 305 | 379 | -74 |
| 1999-06-11 | @ MON | 60 | L 4-5 | 25-35 | 5 | 7,067 | Bobby Witt | Miguel Batista | Miguel Batista | Bobby Witt | Ugueth Urbina | 309 | 384 | -75 |
| 1999-06-12 | @ MON | 61 | W 5-3 | 26-35 | 5 | 9,307 | Mickey Callaway | Dustin Hermanson | Mickey Callaway | Dustin Hermanson | Roberto Hernandez | 314 | 387 | -73 |
| 1999-06-13 | @ MON | 62 | L 0-4 | 26-36 | 5 | 7,234 | Bryan Rekar | Carl Pavano | Carl Pavano | Bryan Rekar | | 314 | 391 | -77 |
| 1999-06-14 | @ CHA | 63 | L 7-9 | 26-37 | 5 | 15,457 | Wilson Alvarez | John Snyder | John Snyder | Wilson Alvarez | Bob Howry | 321 | 400 | -79 |
| 1999-06-15 | @ CHA | 64 | W 3-2 | 27-37 | 5 | 11,347 | Ryan Rupe | James Baldwin | Ryan Rupe | James Baldwin | Roberto Hernandez | 324 | 402 | -78 |
| 1999-06-16 | @ CHA | 65 | L 2-3 | 27-38 | 5 | 10,903 | Bobby Witt | Jim Parque | Sean Lowe | Norm Charlton | | 326 | 405 | -79 |
| 1999-06-18 | @ MIN | 66 | L 5-8 | 27-39 | 5 | 24,157 | Mickey Callaway | Mike Lincoln | Bob Wells | Scott Aldred | Mike Trombley | 331 | 413 | -82 |
| 1999-06-19 | @ MIN | 67 | W 4-3 | 28-39 | 5 | 16,823 | Bryan Rekar | Brad Radke | Bryan Rekar | Brad Radke | Roberto Hernandez | 335 | 416 | -81 |
| 1999-06-20 | @ MIN | 68 | W 6-5 | 29-39 | 5 | 15,413 | Wilson Alvarez | Eric Milton | Alan Newman | Mike Trombley | | 341 | 421 | -80 |
| 1999-06-21 | @ MIN | 69 | W 3-2 | 30-39 | 5 | 13,878 | Ryan Rupe | Joe Mays | Ryan Rupe | Rob Radlosky | Roberto Hernandez | 344 | 423 | -79 |
| 1999-06-22 | vs NYA | 70 | L 0-7 | 30-40 | 5 | 30,290 | Bobby Witt | Orlando Hernandez | Orlando Hernandez | Bobby Witt | | 344 | 430 | -86 |
| 1999-06-23 | vs NYA | 71 | L 4-12 | 31-40 | 5 | 30,474 | Dave Eiland | Roger Clemens | Roger Clemens | Dave Eiland | | 348 | 442 | -94 |
| 1999-06-24 | vs NYA | 72 | L 3-7 | 31-41 | 5 | 30,499 | Bryan Rekar | Andy Pettitte | Andy Pettitte | Bryan Rekar | Ramiro Mendoza | 351 | 449 | -98 |
| 1999-06-25 | vs TOR | 73 | W 11-4 | 31-42 | 5 | 18,633 | Wilson Alvarez | David Wells | Wilson Alvarez | David Wells | | 362 | 453 | -91 |
| 1999-06-26 | vs TOR | 74 | W 5-2 | 32-42 | 5 | 22,062 | Ryan Rupe | Joey Hamilton | Ryan Rupe | Joey Hamilton | Roberto Hernandez | 367 | 455 | -88 |
| 1999-06-27 | vs TOR | 75 | W 8-0 | 33-42 | 5 | 20,556 | Bobby Witt | Kelvim Escobar | Bobby Witt | Kelvim Escobar | | 375 | 455 | -80 |
| 1999-06-28 | vs TOR | 76 | L 2-3 | 33-43 | 5 | 17,727 | Dave Eiland | Chris Carpenter | Chris Carpenter | Dave Eiland | Billy Koch | 377 | 458 | -81 |
| 1999-06-30 | @ BOS | 77 | W 11-10 | 34-43 | 5 | 27,961 | Bryan Rekar | Mark Portugal | Roberto Hernandez | John Wasdin | | 388 | 468 | -80 |
| 1999-07-01 | @ BOS | 78 | W 12-3 | 34-44 | 5 | 29,270 | Wilson Alvarez | Jin Ho Cho | Wilson Alvarez | Jin Ho Cho | | 400 | 471 | -71 |
| 1999-07-02 | @ TOR | 79 | W 8-7 | 35-44 | 5 | 23,109 | Ryan Rupe | Kelvim Escobar | Scott Aldred | Kelvim Escobar | Roberto Hernandez | 408 | 478 | -70 |
| 1999-07-03 | @ TOR | 80 | L 0-5 | 35-45 | 5 | 25,344 | Bobby Witt | Chris Carpenter | Chris Carpenter | Bobby Witt | | 408 | 483 | -75 |
| 1999-07-04 | @ TOR | 81 | L 3-6 | 35-46 | 5 | 24,639 | Dave Eiland | Pat Hentgen | Pat Hentgen | Rick White | Billy Koch | 411 | 489 | -78 |
| 1999-07-05 | vs BOS | 82 | L 2-4 | 35-47 | 5 | 21,967 | Bryan Rekar | Mark Portugal | Mark Portugal | Bryan Rekar | Tim Wakefield | 413 | 493 | -80 |
| 1999-07-06 | vs BOS | 83 | W 6-4 | 36-47 | 5 | 17,309 | Wilson Alvarez | Jin Ho Cho | Albie Lopez | John Wasdin | Roberto Hernandez | 419 | 497 | -78 |
| 1999-07-07 | vs BOS | 84 | W 3-2 | 37-47 | 5 | 20,959 | Dave Eiland | Pedro Martinez | Dave Eiland | Pedro Martinez | Roberto Hernandez | 422 | 499 | -77 |
| 1999-07-08 | vs BOS | 85 | W 3-2 | 38-47 | 5 | 21,160 | Bobby Witt | Brian Rose | Bobby Witt | Brian Rose | Roberto Hernandez | 425 | 501 | -76 |
| 1999-07-09 | @ FLO | 86 | L 4-11 | 39-47 | 5 | 17,976 | Ryan Rupe | Livan Hernandez | Livan Hernandez | Ryan Rupe | | 429 | 512 | -83 |
| 1999-07-10 | @ FLO | 87 | W 9-8 | 40-47 | 5 | 26,516 | Bryan Rekar | Dennis Springer | Bryan Rekar | Dennis Springer | Roberto Hernandez | 438 | 520 | -82 |
| 1999-07-11 | @ FLO | 88 | L 2-3 | 40-48 | 5 | 19,984 | Wilson Alvarez | Alex Fernandez | Alex Fernandez | Wilson Alvarez | Antonio Alfonseca | 440 | 523 | -83 |
| 1999-07-15 | vs NYN | 89 | L 7-8 | 40-49 | 5 | 20,905 | Rolando Arrojo | Al Leiter | Armando Benitez | Norm Charlton | | 447 | 531 | -84 |
| 1999-07-16 | vs NYN | 90 | L 7-9 | 40-50 | 5 | 22,858 | Bobby Witt | Rick Reed | Rick Reed | Dave Eiland | Dennis Cook | 454 | 540 | -86 |
| 1999-07-17 | vs NYN | 91 | W 3-2 | 41-50 | 5 | 40,186 | Wilson Alvarez | Orel Hershiser | Wilson Alvarez | Orel Hershiser | Roberto Hernandez | 457 | 542 | -85 |
| 1999-07-18 | vs PHI | 92 | L 2-3 | 41-51 | 5 | 20,075 | Ryan Rupe | Curt Schilling | Curt Schilling | Albie Lopez | | 459 | 545 | -86 |
| 1999-07-19 | vs PHI | 93 | L 3-16 | 42-51 | 5 | 17,600 | Bryan Rekar | Chad Ogea | Chad Ogea | Bryan Rekar | | 462 | 561 | -99 |
| 1999-07-20 | vs PHI | 94 | W 5-4 | 43-51 | 5 | 30,868 | Rolando Arrojo | Paul Byrd | Norm Charlton | Steve Schrenk | | 467 | 565 | -98 |
| 1999-07-21 | @ NYA | 95 | L 3-4 | 43-52 | 5 | 27,566 | Bobby Witt | Orlando Hernandez | Orlando Hernandez | Bobby Witt | Mariano Rivera | 470 | 569 | -99 |
| 1999-07-22 | @ NYA | 96 | L 4-5 | 43-53 | 5 | 40,557 | Rick White | Andy Pettitte | Andy Pettitte | Bryan Rekar | Mariano Rivera | 474 | 574 | -100 |
| 1999-07-23 | vs TEX | 97 | L 8-11 | 44-53 | 5 | 18,960 | Ryan Rupe | Mike Morgan | Danny Kolb | Ryan Rupe | | 482 | 585 | -103 |
| 1999-07-24 | vs TEX | 98 | L 3-5 | 44-54 | 5 | 22,780 | Dave Eiland | Esteban Loaiza | Esteban Loaiza | Alan Newman | John Wetteland | 485 | 590 | -105 |
| 1999-07-25 | vs TEX | 99 | L 3-4 | 44-55 | 5 | 21,202 | Rolando Arrojo | Rick Helling | Rick Helling | Rolando Arrojo | John Wetteland | 488 | 594 | -106 |
| 1999-07-26 | vs ANA | 100 | W 7-0 | 45-55 | 5 | 15,596 | Bobby Witt | Omar Olivares | Bobby Witt | Omar Olivares | | 495 | 594 | -99 |
| 1999-07-27 | vs ANA | 101 | L 5-10 | 46-55 | 5 | 15,702 | Mickey Callaway | Steve Sparks | Mike Magnante | Mickey Callaway | | 500 | 604 | -104 |
| 1999-07-28 | vs ANA | 102 | W 4-1 | 47-55 | 5 | 18,336 | Ryan Rupe | Jack McDowell | Ryan Rupe | Jack McDowell | Roberto Hernandez | 504 | 605 | -101 |
| 1999-07-30 | @ OAK | 103 | L 1-4 | 47-56 | 5 | 9,269 | Dave Eiland | Mike Oquist | Mike Oquist | Dave Eiland | Billy Taylor | 505 | 609 | -104 |
| 1999-07-31 | @ OAK | 104 | L 1-5 | 47-57 | 5 | 20,081 | Rolando Arrojo | Omar Olivares | Omar Olivares | Rolando Arrojo | Doug Jones | 506 | 614 | -108 |
| 1999-08-01 | @ OAK | 105 | L 6-10 | 48-57 | 5 | 24,951 | Bobby Witt | Gil Heredia | Gil Heredia | Bobby Witt | T.J. Mathews | 512 | 624 | -112 |
| 1999-08-02 | @ SEA | 106 | L 0-4 | 48-58 | 5 | 45,118 | Mickey Callaway | Freddy Garcia | Freddy Garcia | Mickey Callaway | Jose Paniagua | 512 | 628 | -116 |
| 1999-08-03 | @ SEA | 107 | L 2-5 | 48-59 | 5 | 37,180 | Ryan Rupe | John Halama | John Halama | Ryan Rupe | Jose Mesa | 514 | 633 | -119 |
| 1999-08-04 | @ SEA | 108 | W 7-1 | 49-59 | 5 | 42,336 | Dave Eiland | Gil Meche | Dave Eiland | Gil Meche | | 521 | 634 | -113 |
| 1999-08-06 | vs CLE | 109 | W 4-2 | 50-59 | 5 | 34,623 | Rolando Arrojo | Dave Burba | Esteban Yan | Dave Burba | Roberto Hernandez | 525 | 636 | -111 |
| 1999-08-07 | vs CLE | 110 | L 10-15 | 50-60 | 5 | 39,512 | Bobby Witt | Charles Nagy | Charles Nagy | Bobby Witt | | 535 | 651 | -116 |
| 1999-08-08 | vs CLE | 111 | W 5-3 | 51-60 | 5 | 33,052 | Wilson Alvarez | Jaret Wright | Wilson Alvarez | Jaret Wright | Roberto Hernandez | 540 | 654 | -114 |
| 1999-08-09 | vs BAL | 112 | W 10-9 | 51-61 | 5 | 17,796 | Ryan Rupe | Jason Johnson | Ryan Rupe | Jason Johnson | Roberto Hernandez | 550 | 663 | -113 |
| 1999-08-10 | vs BAL | 113 | L 1-17 | 51-62 | 5 | 17,848 | Dave Eiland | Sidney Ponson | Sidney Ponson | Dave Eiland | | 551 | 680 | -129 |
| 1999-08-11 | vs BAL | 114 | L 2-4 | 51-63 | 5 | 17,824 | Rolando Arrojo | Mike Mussina | Mike Mussina | Rolando Arrojo | Mike Timlin | 553 | 684 | -131 |
| 1999-08-12 | @ KCA | 115 | W 7-6 | 52-63 | 5 | 16,201 | Bobby Witt | Dan Reichert | Bobby Witt | Dan Reichert | Roberto Hernandez | 560 | 690 | -130 |
| 1999-08-13 | @ KCA | 116 | L 1-2 | 52-64 | 5 | 23,835 | Wilson Alvarez | Blake Stein | Scott Service | Esteban Yan | | 561 | 692 | -131 |
| 1999-08-14 | @ KCA | 117 | W 11-4 | 52-65 | 5 | 20,684 | Ryan Rupe | Jeff Suppan | Ryan Rupe | Jeff Suppan | | 572 | 696 | -124 |
| 1999-08-15 | @ KCA | 118 | W 5-3 | 53-65 | 5 | 19,162 | Dave Eiland | Jay Witasick | Dave Eiland | Mac Suzuki | Roberto Hernandez | 577 | 699 | -122 |
| 1999-08-16 | @ DET | 119 | W 9-1 | 54-65 | 5 | 21,102 | Rolando Arrojo | Jeff Weaver | Rolando Arrojo | Jeff Weaver | | 586 | 700 | -114 |
| 1999-08-17 | @ DET | 120 | L 1-3 | 54-66 | 5 | 19,418 | Bobby Witt | Dave Mlicki | Dave Mlicki | Bobby Witt | Todd Jones | 587 | 703 | -116 |
| 1999-08-18 | @ DET | 121 | W 4-0 | 55-66 | 5 | 21,311 | Wilson Alvarez | Dave Borkowski | Wilson Alvarez | Dave Borkowski | Albie Lopez | 591 | 703 | -112 |
| 1999-08-20 | vs KCA | 122 | W 5-4 | 56-66 | 5 | 18,396 | Ryan Rupe | Jeff Suppan | Roberto Hernandez | Scott Service | | 596 | 707 | -111 |
| 1999-08-21 | vs KCA | 123 | W 8-2 | 57-66 | 6 | 35,769 | Dave Eiland | Jay Witasick | Dave Eiland | Jay Witasick | | 604 | 709 | -105 |
| 1999-08-22 | vs KCA | 124 | W 2-1 | 58-66 | 5 | 27,864 | Rolando Arrojo | Jose Rosado | Rolando Arrojo | Jose Rosado | | 606 | 710 | -104 |
| 1999-08-23 | vs CHA | 125 | L 2-10 | 59-66 | 5 | 15,386 | Bobby Witt | James Baldwin | James Baldwin | Bobby Witt | | 608 | 720 | -112 |
| 1999-08-24 | vs CHA | 126 | W 6-5 | 60-66 | 5 | 15,425 | Wilson Alvarez | Jim Parque | Wilson Alvarez | Jim Parque | Roberto Hernandez | 614 | 725 | -111 |
| 1999-08-25 | vs CHA | 127 | L 1-6 | 60-67 | 5 | 15,468 | Ryan Rupe | Carlos Castillo | Keith Foulke | Ryan Rupe | | 615 | 731 | -116 |
| 1999-08-26 | vs CHA | 128 | W 9-7 | 61-67 | 5 | 16,475 | Dave Eiland | John Snyder | Rick White | John Snyder | Roberto Hernandez | 624 | 738 | -114 |
| 1999-08-27 | @ CLE | 129 | L 1-2 | 61-68 | 5 | 43,303 | Rolando Arrojo | Dave Burba | Dave Burba | Rolando Arrojo | Michael Jackson | 625 | 740 | -115 |
| 1999-08-28 | @ CLE | 130 | L 0-3 | 61-69 | 5 | 43,190 | Bobby Witt | Charles Nagy | Charles Nagy | Bobby Witt | Michael Jackson | 625 | 743 | -118 |
| 1999-08-29 | @ CLE | 131 | W 6-4 | 62-69 | 5 | 43,151 | Wilson Alvarez | Chris Haney | Wilson Alvarez | Chris Haney | Roberto Hernandez | 631 | 747 | -116 |
| 1999-08-31 | @ BAL | 132 | W 3-0 | 63-69 | 5 | 36,223 | Ryan Rupe | Sidney Ponson | Ryan Rupe | Sidney Ponson | Roberto Hernandez | 634 | 747 | -113 |
| 1999-09-01 | @ BAL | 133 | L 1-3 | 63-70 | 5 | 37,009 | Dan Wheeler | Doug Johns | Doug Johns | Dan Wheeler | Mike Timlin | 635 | 750 | -115 |
| 1999-09-02 | @ BAL | 134 | L 6-11 | 64-70 | 5 | 39,172 | Rolando Arrojo | Scott Erickson | Scott Erickson | Rolando Arrojo | | 641 | 761 | -120 |
| 1999-09-03 | vs MIN | 135 | W 4-2 | 65-70 | 5 | 15,355 | Bobby Witt | LaTroy Hawkins | Norm Charlton | Eddie Guardado | Roberto Hernandez | 645 | 763 | -118 |
| 1999-09-04 | vs MIN | 136 | W 11-3 | 65-71 | 5 | 17,805 | Wilson Alvarez | Jason Ryan | Albie Lopez | Travis Miller | | 656 | 766 | -110 |
| 1999-09-05 | vs MIN | 137 | L 1-4 | 65-72 | 5 | 17,480 | Ryan Rupe | Brad Radke | Brad Radke | Ryan Rupe | | 657 | 770 | -113 |
| 1999-09-06 | vs MIN | 138 | L 7-13 | 66-72 | 5 | 16,929 | Dan Wheeler | Eric Milton | Hector Carrasco | Rick White | | 664 | 783 | -119 |
| 1999-09-08 | vs DET | 139 | L 1-5 | 66-73 | 5 | 14,887 | Bobby Witt | Dave Mlicki | Dave Mlicki | Bobby Witt | | 665 | 788 | -123 |
| 1999-09-09 | vs DET | 140 | W 5-3 | 67-73 | 5 | 15,056 | Rolando Arrojo | C.J. Nitkowski | Rolando Arrojo | C.J. Nitkowski | Roberto Hernandez | 670 | 791 | -121 |
| 1999-09-10 | vs OAK | 141 | L 2-7 | 67-74 | 5 | 16,182 | Wilson Alvarez | Tim Hudson | Tim Hudson | Wilson Alvarez | | 672 | 798 | -126 |
| 1999-09-11 | vs OAK | 142 | L 4-5 | 67-75 | 5 | 25,362 | Ryan Rupe | Omar Olivares | Omar Olivares | Ryan Rupe | Doug Jones | 676 | 803 | -127 |
| 1999-09-12 | vs OAK | 143 | L 3-4 | 67-76 | 5 | 25,147 | Dan Wheeler | Gil Heredia | Gil Heredia | Dan Wheeler | Jason Isringhausen | 679 | 807 | -128 |
| 1999-09-13 | vs OAK | 144 | L 3-8 | 67-77 | 5 | 14,936 | Bobby Witt | Kevin Appier | Kevin Appier | Bobby Witt | | 682 | 815 | -133 |
| 1999-09-14 | vs SEA | 145 | L 1-5 | 67-78 | 5 | 15,154 | Rolando Arrojo | Jamie Moyer | Jamie Moyer | Rolando Arrojo | | 683 | 820 | -137 |
| 1999-09-15 | vs SEA | 146 | W 8-4 | 68-78 | 5 | 15,542 | Wilson Alvarez | Ken Cloude | Albie Lopez | Frankie Rodriguez | | 691 | 824 | -133 |
| 1999-09-16 | vs SEA | 147 | L 3-5 | 68-79 | 5 | 15,817 | Ryan Rupe | Freddy Garcia | Freddy Garcia | Esteban Yan | Jose Mesa | 694 | 829 | -135 |
| 1999-09-17 | @ TEX | 148 | W 7-5 | 69-79 | 5 | 33,695 | Dan Wheeler | Rick Helling | Alan Newman | Rick Helling | Roberto Hernandez | 701 | 834 | -133 |
| 1999-09-18 | @ TEX | 149 | L 1-6 | 69-80 | 5 | 36,820 | Bobby Witt | Aaron Sele | Aaron Sele | Bobby Witt | | 702 | 840 | -138 |
| 1999-09-19 | @ TEX | 150 | W 15-2 | 69-81 | 5 | 24,930 | Rolando Arrojo | John Burkett | Rolando Arrojo | John Burkett | | 717 | 842 | -125 |
| 1999-09-20 | @ ANA | 151 | L 5-10 | 70-81 | 5 | 16,165 | Wilson Alvarez | Chuck Finley | Chuck Finley | Wilson Alvarez | | 722 | 852 | -130 |
| 1999-09-21 | @ ANA | 152 | L 5-7 | 70-82 | 5 | 16,486 | Dave Eiland | Ramon Ortiz | Ramon Ortiz | Dave Eiland | Troy Percival | 727 | 859 | -132 |
| 1999-09-22 | @ ANA | 153 | L 5-8 | 70-83 | 5 | 16,801 | Dan Wheeler | Jarrod Washburn | Jarrod Washburn | Dan Wheeler | | 732 | 867 | -135 |
| 1999-09-24 | @ NYA | 154 | L 3-4 | 70-84 | 5 | 44,932 | Bobby Witt | Orlando Hernandez | Mike Stanton | Norm Charlton | | 735 | 871 | -136 |
| 1999-09-25 | @ NYA | 155 | W 2-1 | 71-84 | 5 | 50,403 | Rolando Arrojo | David Cone | Rolando Arrojo | David Cone | Roberto Hernandez | 737 | 872 | -135 |
| 1999-09-26 | @ NYA | 156 | W 6-5 | 72-84 | 5 | 49,458 | Wilson Alvarez | Andy Pettitte | Cory Lidle | Ramiro Mendoza | Roberto Hernandez | 743 | 877 | -134 |
| 1999-09-27 | @ NYA | 157 | W 10-6 | 72-85 | 5 | 41,355 | Dave Eiland | Hideki Irabu | Mike Duvall | Hideki Irabu | Jeff Sparks | 753 | 883 | -130 |
| 1999-09-28 | vs TOR | 158 | L 2-8 | 72-86 | 5 | 19,781 | Dan Wheeler | David Wells | David Wells | Dan Wheeler | | 755 | 891 | -136 |
| 1999-09-29 | vs TOR | 159 | L 2-6 | 72-87 | 6 | 22,180 | Bobby Witt | Kelvim Escobar | Kelvim Escobar | Bobby Witt | | 757 | 897 | -140 |
| 1999-10-01 | vs NYA | 160 | L 7-11 | 73-87 | 5 | 27,248 | Rolando Arrojo | Andy Pettitte | Ramiro Mendoza | Rolando Arrojo | Mariano Rivera | 764 | 908 | -144 |
| 1999-10-02 | vs NYA | 161 | L 2-3 | 73-88 | 5 | 40,756 | Wilson Alvarez | David Cone | David Cone | Wilson Alvarez | Mariano Rivera | 766 | 911 | -145 |
| 1999-10-03 | vs NYA | 162 | W 6-2 | 74-88 | 5 | 31,292 | Cory Lidle | Jeff Juden | Eddie Gaillard | Jeff Juden | Roberto Hernandez | 772 | 913 | -141 |