| 1999-04-05 | vs NYA | 1 | W 5-3 | 1-0 | 1 | 46,380 | Gil Heredia | Roger Clemens | T.J. Mathews | Mike Stanton | | 5 | 3 | 2 |
| 1999-04-06 | vs NYA | 2 | L 4-7 | 1-1 | 3 | 15,579 | Tom Candiotti | Orlando Hernandez | Orlando Hernandez | Tom Candiotti | Mariano Rivera | 9 | 10 | -1 |
| 1999-04-07 | vs NYA | 3 | L 0-4 | 1-2 | 4 | 18,846 | Jimmy Haynes | Ramiro Mendoza | Ramiro Mendoza | Jimmy Haynes | | 9 | 14 | -5 |
| 1999-04-09 | @ SEA | 4 | L 1-6 | 1-3 | 4 | 24,823 | Kenny Rogers | Butch Henry | Butch Henry | Kenny Rogers | | 10 | 20 | -10 |
| 1999-04-10 | @ SEA | 5 | W 11-4 | 1-4 | 4 | 35,991 | Gil Heredia | Jeff Fassero | Gil Heredia | Jeff Fassero | | 21 | 24 | -3 |
| 1999-04-11 | @ SEA | 6 | L 8-11 | 2-4 | 4 | 24,036 | Tom Candiotti | Jamie Moyer | Jamie Moyer | Tom Candiotti | | 29 | 35 | -6 |
| 1999-04-12 | @ SEA | 7 | L 3-6 | 2-5 | 4 | 24,650 | Jimmy Haynes | Freddy Garcia | Freddy Garcia | Jimmy Haynes | Jose Mesa | 32 | 41 | -9 |
| 1999-04-13 | vs ANA | 8 | W 3-2 | 3-5 | 4 | 5,377 | Mike Oquist | Steve Sparks | Mike Oquist | Steve Sparks | Billy Taylor | 35 | 43 | -8 |
| 1999-04-14 | vs ANA | 9 | W 6-5 | 4-5 | 3 | 8,377 | Kenny Rogers | Chuck Finley | T.J. Mathews | Chuck Finley | Billy Taylor | 41 | 48 | -7 |
| 1999-04-15 | vs ANA | 10 | L 1-12 | 4-6 | 4 | 7,148 | Gil Heredia | Omar Olivares | Omar Olivares | Gil Heredia | | 42 | 60 | -18 |
| 1999-04-16 | vs TEX | 11 | W 8-2 | 5-6 | 4 | 9,158 | Tom Candiotti | Aaron Sele | Tom Candiotti | Aaron Sele | | 50 | 62 | -12 |
| 1999-04-17 | vs TEX | 12 | W 11-3 | 5-7 | 4 | 16,271 | Jimmy Haynes | Mark Clark | Jimmy Haynes | Mark Clark | | 61 | 65 | -4 |
| 1999-04-18 | vs TEX | 13 | L 2-6 | 5-8 | 4 | 14,460 | Mike Oquist | Mike Morgan | Mike Morgan | Mike Oquist | | 63 | 71 | -8 |
| 1999-04-20 | @ CLE | 14 | L 1-5 | 5-9 | 4 | 42,954 | Kenny Rogers | Bartolo Colon | Bartolo Colon | Kenny Rogers | | 64 | 76 | -12 |
| 1999-04-21 | @ CLE | 15 | L 4-5 | 5-10 | 4 | 41,933 | Gil Heredia | Dwight Gooden | Steve Reed | Billy Taylor | | 68 | 81 | -13 |
| 1999-04-22 | @ CLE | 16 | W 4-1 | 6-10 | 3 | 42,937 | Tom Candiotti | Charles Nagy | Tom Candiotti | Charles Nagy | Billy Taylor | 72 | 82 | -10 |
| 1999-04-23 | @ BAL | 17 | L 4-7 | 6-11 | 4 | 42,978 | Jimmy Haynes | Juan Guzman | Mike Fetters | Jimmy Haynes | | 76 | 89 | -13 |
| 1999-04-24 | @ BAL | 18 | W 3-0 | 7-11 | 3 | 41,540 | Mike Oquist | Scott Erickson | Mike Oquist | Scott Erickson | Billy Taylor | 79 | 89 | -10 |
| 1999-04-25 | @ BAL | 19 | W 11-10 | 8-11 | 3 | 45,675 | Kenny Rogers | Rocky Coppinger | Brad Rigby | Mike Timlin | Billy Taylor | 90 | 99 | -9 |
| 1999-04-26 | vs CLE | 20 | L 4-5 | 8-12 | 3 | 7,646 | Gil Heredia | Dwight Gooden | Steve Karsay | Billy Taylor | Michael Jackson | 94 | 104 | -10 |
| 1999-04-27 | vs CLE | 21 | L 5-8 | 8-13 | 3 | 7,161 | Tom Candiotti | Charles Nagy | Charles Nagy | Tom Candiotti | Michael Jackson | 99 | 112 | -13 |
| 1999-04-28 | vs CLE | 22 | L 1-4 | 8-14 | 4 | 9,555 | Jimmy Haynes | Jaret Wright | Jaret Wright | Jimmy Haynes | Michael Jackson | 100 | 116 | -16 |
| 1999-04-29 | vs CLE | 23 | L 3-8 | 8-15 | 4 | 10,115 | Mike Oquist | Dave Burba | Dave Burba | Mike Oquist | | 103 | 124 | -21 |
| 1999-04-30 | vs BOS | 24 | W 13-9 | 8-16 | 4 | 10,063 | Kenny Rogers | Kip Gross | T.J. Mathews | Derek Lowe | | 116 | 133 | -17 |
| 1999-05-01 | vs BOS | 25 | L 2-7 | 8-17 | 4 | 30,353 | Gil Heredia | Pedro Martinez | Pedro Martinez | Gil Heredia | | 118 | 140 | -22 |
| 1999-05-02 | vs BOS | 26 | W 7-5 | 9-17 | 4 | 17,388 | Tom Candiotti | Tim Wakefield | Doug Jones | Tim Harikkala | Billy Taylor | 125 | 145 | -20 |
| 1999-05-03 | vs BOS | 27 | W 12-11 | 10-17 | 4 | 8,221 | Jimmy Haynes | Mark Portugal | T.J. Mathews | Kip Gross | | 137 | 156 | -19 |
| 1999-05-04 | @ TOR | 28 | W 13-4 | 10-18 | 4 | 20,258 | Mike Oquist | Roy Halladay | Mike Oquist | Roy Halladay | Doug Jones | 150 | 160 | -10 |
| 1999-05-05 | @ TOR | 29 | W 8-2 | 11-18 | 4 | 20,314 | Kenny Rogers | Kelvim Escobar | Kenny Rogers | Kelvim Escobar | | 158 | 162 | -4 |
| 1999-05-06 | @ TOR | 30 | W 3-2 | 12-18 | 4 | 20,310 | Gil Heredia | Chris Carpenter | Gil Heredia | Chris Carpenter | Billy Taylor | 161 | 164 | -3 |
| 1999-05-07 | @ CHA | 31 | L 1-7 | 12-19 | 4 | 11,181 | Tom Candiotti | Jim Parque | Jim Parque | Tom Candiotti | | 162 | 171 | -9 |
| 1999-05-08 | @ CHA | 32 | L 3-5 | 12-20 | 4 | 15,489 | Jimmy Haynes | John Snyder | John Snyder | Jimmy Haynes | Bob Howry | 165 | 176 | -11 |
| 1999-05-09 | @ CHA | 33 | W 3-0 | 13-20 | 3 | 12,652 | Mike Oquist | Mike Sirotka | Mike Oquist | Mike Sirotka | Doug Jones | 168 | 176 | -8 |
| 1999-05-11 | @ DET | 34 | W 6-2 | 14-20 | 3 | 12,411 | Kenny Rogers | Jeff Weaver | Brad Rigby | Jeff Weaver | | 174 | 178 | -4 |
| 1999-05-12 | @ DET | 35 | W 2-1 | 15-20 | 3 | 13,565 | Gil Heredia | Justin Thompson | Gil Heredia | Justin Thompson | Billy Taylor | 176 | 179 | -3 |
| 1999-05-14 | vs MIN | 36 | W 7-5 | 16-20 | 4 | 8,145 | Tom Candiotti | Mike Lincoln | Tim Worrell | Mike Lincoln | Billy Taylor | 183 | 184 | -1 |
| 1999-05-15 | vs MIN | 37 | W 6-5 | 17-20 | 2 | 18,016 | Mike Oquist | LaTroy Hawkins | T.J. Mathews | Eddie Guardado | | 189 | 189 | 0 |
| 1999-05-16 | vs MIN | 38 | W 4-2 | 18-20 | 2 | 31,804 | Jimmy Haynes | Brad Radke | Jimmy Haynes | Brad Radke | Billy Taylor | 193 | 191 | 2 |
| 1999-05-18 | @ KCA | 39 | L 3-13 | 19-20 | 2 | 14,212 | Gil Heredia | Kevin Appier | Kevin Appier | Gil Heredia | | 196 | 204 | -8 |
| 1999-05-19 | @ KCA | 40 | L 3-14 | 20-20 | 2 | 13,727 | Tom Candiotti | Jose Rosado | Jose Rosado | Tom Candiotti | Terry Mathews | 199 | 218 | -19 |
| 1999-05-20 | @ KCA | 41 | L 1-7 | 20-21 | 2 | 15,172 | Mike Oquist | Jeff Suppan | Jeff Suppan | Mike Oquist | | 200 | 225 | -25 |
| 1999-05-21 | @ MIN | 42 | L 1-2 | 20-22 | 3 | 14,433 | Jimmy Haynes | LaTroy Hawkins | Travis Miller | Doug Jones | | 201 | 227 | -26 |
| 1999-05-22 | @ MIN | 43 | L 1-2 | 20-23 | 4 | 15,381 | Kenny Rogers | Brad Radke | Bob Wells | Brad Rigby | | 202 | 229 | -27 |
| 1999-05-23 | @ MIN | 44 | L 3-8 | 20-24 | 4 | 12,881 | Gil Heredia | Eric Milton | Eric Milton | Gil Heredia | | 205 | 237 | -32 |
| 1999-05-25 | vs KCA | 45 | W 5-3 | 21-24 | 4 | 6,839 | Mike Oquist | Jose Rosado | Mike Oquist | Jose Rosado | Doug Jones | 210 | 240 | -30 |
| 1999-05-26 | vs KCA | 46 | W 3-1 | 22-24 | 3 | 9,216 | Jimmy Haynes | Jeff Suppan | Jimmy Haynes | Jeff Suppan | Billy Taylor | 213 | 241 | -28 |
| 1999-05-27 | vs KCA | 47 | W 6-1 | 23-24 | 2 | 13,180 | Kenny Rogers | Jay Witasick | Kenny Rogers | Jay Witasick | | 219 | 242 | -23 |
| 1999-05-28 | vs BAL | 48 | W 2-1 | 24-24 | 2 | 7,443 | Tom Candiotti | Mike Mussina | Tom Candiotti | Mike Mussina | Billy Taylor | 221 | 243 | -22 |
| 1999-05-29 | vs BAL | 49 | L 5-7 | 24-25 | 3 | 26,247 | Gil Heredia | Jason Johnson | Doug Johns | T.J. Mathews | Arthur Rhodes | 226 | 250 | -24 |
| 1999-05-30 | vs BAL | 50 | W 11-5 | 24-26 | 4 | 18,320 | Mike Oquist | Scott Erickson | Brad Rigby | Scott Erickson | | 237 | 255 | -18 |
| 1999-05-31 | vs TBA | 51 | W 10-7 | 24-27 | 4 | 10,444 | Jimmy Haynes | Bobby Witt | Buddy Groom | Esteban Yan | | 247 | 262 | -15 |
| 1999-06-01 | vs TBA | 52 | W 5-2 | 25-27 | 3 | 7,170 | Kenny Rogers | Dave Eiland | Kenny Rogers | Dave Eiland | Billy Taylor | 252 | 264 | -12 |
| 1999-06-02 | vs TBA | 53 | L 6-7 | 25-28 | 4 | 17,505 | Tom Candiotti | Wilson Alvarez | Esteban Yan | T.J. Mathews | Roberto Hernandez | 258 | 271 | -13 |
| 1999-06-04 | @ SFN | 54 | L 3-4 | 25-29 | 4 | 32,456 | Gil Heredia | Chris Brock | Jerry Spradlin | Billy Taylor | | 261 | 275 | -14 |
| 1999-06-05 | @ SFN | 55 | L 0-8 | 25-30 | 4 | 31,959 | Mike Oquist | Kirk Rueter | Kirk Rueter | Mike Oquist | | 261 | 283 | -22 |
| 1999-06-06 | @ SFN | 56 | W 7-6 | 26-30 | 4 | 40,154 | Kenny Rogers | Mark Gardner | Buddy Groom | John Johnstone | Billy Taylor | 268 | 289 | -21 |
| 1999-06-08 | @ SDN | 57 | L 3-5 | 26-31 | 4 | 17,195 | Tim Hudson | Heath Murray | Donne Wall | Buddy Groom | Trevor Hoffman | 271 | 294 | -23 |
| 1999-06-09 | @ SDN | 58 | W 3-0 | 27-31 | 3 | 15,896 | Jimmy Haynes | Matt Clement | Jimmy Haynes | Matt Clement | Billy Taylor | 274 | 294 | -20 |
| 1999-06-10 | @ SDN | 59 | L 1-2 | 27-32 | 4 | 20,024 | Gil Heredia | Sterling Hitchcock | Sterling Hitchcock | Gil Heredia | Trevor Hoffman | 275 | 296 | -21 |
| 1999-06-11 | vs LAN | 60 | W 12-6 | 27-33 | 4 | 24,261 | Mike Oquist | Carlos Perez | Mike Oquist | Carlos Perez | T.J. Mathews | 287 | 302 | -15 |
| 1999-06-12 | vs LAN | 61 | W 4-3 | 28-33 | 4 | 31,391 | Kenny Rogers | Ismael Valdez | Kenny Rogers | Ismael Valdez | Billy Taylor | 291 | 305 | -14 |
| 1999-06-13 | vs LAN | 62 | W 9-3 | 29-33 | 3 | 27,973 | Tim Hudson | Darren Dreifort | Tim Hudson | Darren Dreifort | | 300 | 308 | -8 |
| 1999-06-15 | @ CLE | 63 | L 3-8 | 29-34 | 3 | 43,231 | Jimmy Haynes | Jaret Wright | Jaret Wright | Jimmy Haynes | | 303 | 316 | -13 |
| 1999-06-16 | @ CLE | 64 | L 8-9 | 29-35 | 4 | 43,163 | Gil Heredia | Bartolo Colon | Steve Karsay | Billy Taylor | | 311 | 325 | -14 |
| 1999-06-17 | @ CLE | 65 | L 6-10 | 30-35 | 4 | 43,262 | Kenny Rogers | Dwight Gooden | Paul Shuey | Tim Worrell | | 317 | 335 | -18 |
| 1999-06-18 | @ DET | 66 | L 3-8 | 30-36 | 4 | 22,347 | Mike Oquist | Justin Thompson | Justin Thompson | Mike Oquist | | 320 | 343 | -23 |
| 1999-06-19 | @ DET | 67 | W 13-1 | 31-36 | 4 | 24,704 | Tim Hudson | Nelson Cruz | Tim Hudson | Nelson Cruz | | 333 | 344 | -11 |
| 1999-06-20 | @ DET | 68 | W 6-5 | 32-36 | 4 | 25,934 | Jimmy Haynes | Brian Moehler | Jimmy Haynes | Brian Moehler | Billy Taylor | 339 | 349 | -10 |
| 1999-06-21 | @ DET | 69 | L 11-13 | 32-37 | 4 | 16,083 | Gil Heredia | Dave Mlicki | Doug Brocail | Brad Rigby | Todd Jones | 350 | 362 | -12 |
| 1999-06-22 | @ TEX | 70 | W 5-3 | 33-37 | 4 | 35,619 | Kenny Rogers | Aaron Sele | T.J. Mathews | John Wetteland | Billy Taylor | 355 | 365 | -10 |
| 1999-06-23 | @ TEX | 71 | L 6-7 | 33-38 | 4 | 45,995 | Mike Oquist | Mike Morgan | Mike Morgan | Mike Oquist | John Wetteland | 361 | 372 | -11 |
| 1999-06-24 | @ TEX | 72 | L 2-5 | 33-39 | 4 | 39,683 | Tim Hudson | John Burkett | John Burkett | Tim Hudson | John Wetteland | 363 | 377 | -14 |
| 1999-06-25 | @ ANA | 73 | L 3-4 | 33-40 | 4 | 29,911 | Jimmy Haynes | Omar Olivares | Troy Percival | Doug Jones | | 366 | 381 | -15 |
| 1999-06-26 | @ ANA | 74 | L 4-5 | 33-41 | 4 | 29,957 | Gil Heredia | Tim Belcher | Mike Magnante | Brad Rigby | Troy Percival | 370 | 386 | -16 |
| 1999-06-27 | @ ANA | 75 | L 3-4 | 33-42 | 4 | 31,782 | Kenny Rogers | Steve Sparks | Steve Sparks | Kenny Rogers | Troy Percival | 373 | 390 | -17 |
| 1999-06-29 | vs SEA | 76 | L 1-2 | 33-43 | 4 | 11,762 | Mike Oquist | John Halama | Jose Paniagua | T.J. Mathews | Jose Mesa | 374 | 392 | -18 |
| 1999-06-30 | vs SEA | 77 | W 14-5 | 33-44 | 4 | 17,224 | Tim Hudson | Jeff Fassero | Tim Hudson | Jeff Fassero | | 388 | 397 | -9 |
| 1999-07-01 | vs SEA | 78 | W 5-4 | 34-44 | 4 | 11,632 | Jimmy Haynes | Frankie Rodriguez | Billy Taylor | Jose Paniagua | | 393 | 401 | -8 |
| 1999-07-02 | vs ANA | 79 | L 6-10 | 35-44 | 4 | 8,570 | Kenny Rogers | Steve Sparks | Mark Petkovsek | Chad Harville | | 399 | 411 | -12 |
| 1999-07-03 | vs ANA | 80 | W 9-7 | 36-44 | 4 | 50,916 | Gil Heredia | Chuck Finley | Gil Heredia | Chuck Finley | Billy Taylor | 408 | 418 | -10 |
| 1999-07-04 | vs ANA | 81 | L 2-5 | 36-45 | 4 | 19,721 | Mike Oquist | Omar Olivares | Omar Olivares | Mike Oquist | | 410 | 423 | -13 |
| 1999-07-05 | vs TEX | 82 | W 4-2 | 37-45 | 4 | 7,490 | Tim Hudson | John Burkett | Tim Hudson | John Burkett | Billy Taylor | 414 | 425 | -11 |
| 1999-07-06 | vs TEX | 83 | W 4-0 | 38-45 | 4 | 8,221 | Jimmy Haynes | Ryan Glynn | Jimmy Haynes | Ryan Glynn | | 418 | 425 | -7 |
| 1999-07-07 | vs TEX | 84 | L 4-7 | 38-46 | 4 | 15,566 | Kenny Rogers | Rick Helling | Jeff Zimmerman | Brad Rigby | John Wetteland | 422 | 432 | -10 |
| 1999-07-09 | @ ARI | 85 | W 5-2 | 39-46 | 4 | 33,635 | Gil Heredia | Andy Benes | Gil Heredia | Andy Benes | Billy Taylor | 427 | 434 | -7 |
| 1999-07-10 | @ ARI | 86 | W 2-0 | 40-46 | 4 | 36,042 | Tim Hudson | Randy Johnson | Tim Hudson | Randy Johnson | Billy Taylor | 429 | 434 | -5 |
| 1999-07-11 | @ ARI | 87 | L 4-7 | 40-47 | 4 | 36,632 | Jimmy Haynes | Omar Daal | Omar Daal | Jimmy Haynes | Matt Mantei | 433 | 441 | -8 |
| 1999-07-15 | vs SFN | 88 | W 11-9 | 40-48 | 4 | 29,428 | Kenny Rogers | Shawn Estes | Doug Jones | Robb Nen | | 444 | 450 | -6 |
| 1999-07-16 | vs SFN | 89 | W 4-2 | 41-48 | 4 | 44,671 | Gil Heredia | Russ Ortiz | Gil Heredia | Russ Ortiz | Billy Taylor | 448 | 452 | -4 |
| 1999-07-17 | vs SFN | 90 | L 2-7 | 41-49 | 4 | 51,263 | Tim Hudson | Kirk Rueter | Kirk Rueter | Buddy Groom | | 450 | 459 | -9 |
| 1999-07-18 | vs COL | 91 | W 3-2 | 42-49 | 4 | 15,074 | Jimmy Haynes | Bobby Jones | Jimmy Haynes | Bobby Jones | Billy Taylor | 453 | 461 | -8 |
| 1999-07-19 | vs COL | 92 | W 10-5 | 42-50 | 4 | 9,281 | Mike Oquist | Roberto Ramirez | Tim Worrell | Roberto Ramirez | Doug Jones | 463 | 466 | -3 |
| 1999-07-20 | vs COL | 93 | W 4-3 | 43-50 | 4 | 13,414 | Kenny Rogers | Darryl Kile | Kenny Rogers | Darryl Kile | Billy Taylor | 467 | 469 | -2 |
| 1999-07-21 | @ SEA | 94 | W 13-3 | 43-51 | 4 | 42,223 | Gil Heredia | Jeff Fassero | Gil Heredia | Jeff Fassero | | 480 | 472 | 8 |
| 1999-07-22 | @ SEA | 95 | L 4-5 | 43-52 | 4 | 44,311 | Tim Hudson | Freddy Garcia | Paul Abbott | Doug Jones | | 484 | 477 | 7 |
| 1999-07-23 | @ KCA | 96 | L 7-12 | 44-52 | 4 | 21,325 | Jimmy Haynes | Mac Suzuki | Alvin Morman | Jimmy Haynes | Brian Barber | 491 | 489 | 2 |
| 1999-07-24 | @ KCA | 97 | W 12-2 | 44-53 | 4 | 29,739 | Mike Oquist | Jay Witasick | Mike Oquist | Jay Witasick | | 503 | 491 | 12 |
| 1999-07-25 | @ KCA | 98 | L 11-13 | 44-54 | 4 | 20,454 | Blake Stein | Dan Reichert | Scott Service | Chad Harville | | 514 | 504 | 10 |
| 1999-07-26 | @ MIN | 99 | W 14-7 | 44-55 | 4 | 11,356 | Gil Heredia | Eric Milton | Buddy Groom | Benj Sampson | | 528 | 511 | 17 |
| 1999-07-27 | @ MIN | 100 | L 2-3 | 44-56 | 4 | 11,582 | Tim Hudson | Joe Mays | Joe Mays | Billy Taylor | Eddie Guardado | 530 | 514 | 16 |
| 1999-07-28 | @ MIN | 101 | L 3-5 | 44-57 | 4 | 20,420 | Jimmy Haynes | LaTroy Hawkins | LaTroy Hawkins | Jimmy Haynes | Mike Trombley | 533 | 519 | 14 |
| 1999-07-30 | vs TBA | 102 | W 4-1 | 45-57 | 3 | 9,269 | Mike Oquist | Dave Eiland | Mike Oquist | Dave Eiland | Billy Taylor | 537 | 520 | 17 |
| 1999-07-31 | vs TBA | 103 | W 5-1 | 46-57 | 3 | 20,081 | Omar Olivares | Rolando Arrojo | Omar Olivares | Rolando Arrojo | Doug Jones | 542 | 521 | 21 |
| 1999-08-01 | vs TBA | 104 | W 10-6 | 46-58 | 3 | 24,951 | Gil Heredia | Bobby Witt | Gil Heredia | Bobby Witt | T.J. Mathews | 552 | 527 | 25 |
| 1999-08-02 | vs BAL | 105 | W 7-1 | 47-58 | 3 | 10,178 | Kevin Appier | Scott Erickson | Kevin Appier | Scott Erickson | | 559 | 528 | 31 |
| 1999-08-03 | vs BAL | 106 | W 12-2 | 47-59 | 3 | 10,878 | Tim Hudson | Ricky Bones | Tim Hudson | Ricky Bones | | 571 | 530 | 41 |
| 1999-08-04 | vs BAL | 107 | L 5-9 | 47-60 | 4 | 17,271 | Jimmy Haynes | Jason Johnson | Jason Johnson | Jimmy Haynes | | 576 | 539 | 37 |
| 1999-08-05 | vs CHA | 108 | W 7-6 | 48-60 | 4 | 9,305 | Omar Olivares | Mike Sirotka | T.J. Mathews | Scott Eyre | | 583 | 545 | 38 |
| 1999-08-06 | vs CHA | 109 | W 9-1 | 49-60 | 3 | 11,267 | Gil Heredia | Jaime Navarro | Gil Heredia | Jaime Navarro | | 592 | 546 | 46 |
| 1999-08-07 | vs CHA | 110 | W 11-1 | 50-60 | 3 | 26,091 | Kevin Appier | Jim Parque | Kevin Appier | Jim Parque | | 603 | 547 | 56 |
| 1999-08-08 | vs CHA | 111 | W 7-5 | 51-60 | 3 | 22,821 | Tim Hudson | James Baldwin | Doug Jones | Keith Foulke | | 610 | 552 | 58 |
| 1999-08-09 | vs NYA | 112 | L 8-12 | 52-60 | 3 | 24,896 | Jimmy Haynes | Hideki Irabu | Ramiro Mendoza | Jimmy Haynes | | 618 | 564 | 54 |
| 1999-08-10 | vs NYA | 113 | W 6-1 | 53-60 | 3 | 32,474 | Omar Olivares | Roger Clemens | Omar Olivares | Roger Clemens | Doug Jones | 624 | 565 | 59 |
| 1999-08-11 | vs NYA | 114 | L 3-5 | 53-61 | 3 | 43,683 | Gil Heredia | Orlando Hernandez | Allen Watson | Doug Jones | Mariano Rivera | 627 | 570 | 57 |
| 1999-08-13 | @ TOR | 115 | W 9-8 | 54-61 | 4 | 34,150 | Kevin Appier | Roy Halladay | Kevin Appier | Roy Halladay | Doug Jones | 636 | 578 | 58 |
| 1999-08-14 | @ TOR | 116 | W 13-5 | 54-62 | 3 | 37,113 | Tim Hudson | Joey Hamilton | Tim Hudson | Joey Hamilton | | 649 | 583 | 66 |
| 1999-08-15 | @ TOR | 117 | W 9-5 | 55-62 | 3 | 34,677 | Mike Oquist | Kelvim Escobar | Mike Oquist | Kelvim Escobar | | 658 | 588 | 70 |
| 1999-08-16 | @ BOS | 118 | L 5-6 | 55-63 | 3 | 30,957 | Omar Olivares | Brian Rose | Derek Lowe | Doug Jones | | 663 | 594 | 69 |
| 1999-08-17 | @ BOS | 119 | W 12-1 | 56-63 | 3 | 31,246 | Gil Heredia | Bret Saberhagen | Gil Heredia | Bret Saberhagen | | 675 | 595 | 80 |
| 1999-08-18 | @ BOS | 120 | L 4-7 | 56-64 | 3 | 32,405 | Kevin Appier | Pat Rapp | Rich Garces | Kevin Appier | Derek Lowe | 679 | 602 | 77 |
| 1999-08-19 | @ BOS | 121 | W 6-2 | 57-64 | 3 | 33,393 | Tim Hudson | Pedro Martinez | Tim Hudson | Pedro Martinez | T.J. Mathews | 685 | 604 | 81 |
| 1999-08-20 | vs TOR | 122 | L 0-11 | 57-65 | 3 | 13,335 | Mike Oquist | Joey Hamilton | Joey Hamilton | Mike Oquist | | 685 | 615 | 70 |
| 1999-08-21 | vs TOR | 123 | W 8-4 | 58-65 | 3 | 26,282 | Omar Olivares | Chris Carpenter | Omar Olivares | Chris Carpenter | | 693 | 619 | 74 |
| 1999-08-22 | vs TOR | 124 | W 4-3 | 59-65 | 3 | 23,907 | Gil Heredia | Roy Halladay | Doug Jones | Billy Koch | | 697 | 622 | 75 |
| 1999-08-23 | vs TOR | 125 | L 4-9 | 59-66 | 3 | 10,047 | Kevin Appier | David Wells | David Wells | Kevin Appier | | 701 | 631 | 70 |
| 1999-08-24 | vs CLE | 126 | W 11-10 | 60-66 | 3 | 17,417 | Tim Hudson | Steve Karsay | T.J. Mathews | Paul Shuey | | 712 | 641 | 71 |
| 1999-08-25 | vs CLE | 127 | L 4-12 | 61-66 | 3 | 21,328 | Mike Oquist | Bartolo Colon | Bartolo Colon | Mike Oquist | | 716 | 653 | 63 |
| 1999-08-27 | @ CHA | 128 | W 9-6 | 62-66 | 3 | 14,270 | Omar Olivares | Mike Sirotka | Omar Olivares | Mike Sirotka | Jason Isringhausen | 725 | 659 | 66 |
| 1999-08-28 | @ CHA | 129 | W 7-5 | 63-66 | 3 | 27,121 | Gil Heredia | Jaime Navarro | Gil Heredia | Jaime Navarro | Doug Jones | 732 | 664 | 68 |
| 1999-08-29 | @ CHA | 130 | L 2-7 | 63-67 | 3 | 16,403 | Kevin Appier | James Baldwin | James Baldwin | Kevin Appier | Keith Foulke | 734 | 671 | 63 |
| 1999-08-30 | @ NYA | 131 | L 4-7 | 63-68 | 4 | 32,712 | Tim Hudson | Hideki Irabu | Jeff Nelson | T.J. Mathews | Mariano Rivera | 738 | 678 | 60 |
| 1999-08-31 | @ NYA | 132 | W 3-2 | 64-68 | 3 | 33,746 | Jimmy Haynes | David Cone | Doug Jones | Ramiro Mendoza | Jason Isringhausen | 741 | 680 | 61 |
| 1999-09-01 | @ NYA | 133 | W 7-1 | 65-68 | 3 | 34,468 | Omar Olivares | Roger Clemens | Omar Olivares | Roger Clemens | | 748 | 681 | 67 |
| 1999-09-02 | @ NYA | 134 | L 3-9 | 65-69 | 3 | 33,147 | Gil Heredia | Orlando Hernandez | Orlando Hernandez | Gil Heredia | | 751 | 690 | 61 |
| 1999-09-03 | vs DET | 135 | W 7-4 | 66-69 | 3 | 10,297 | Kevin Appier | C.J. Nitkowski | Kevin Appier | Nelson Cruz | Jason Isringhausen | 758 | 694 | 64 |
| 1999-09-04 | vs DET | 136 | W 2-1 | 67-69 | 3 | 18,323 | Tim Hudson | Brian Moehler | Tim Hudson | Francisco Cordero | | 760 | 695 | 65 |
| 1999-09-05 | vs DET | 137 | L 4-5 | 67-70 | 3 | 20,429 | Jimmy Haynes | Willie Blair | Willie Blair | Jimmy Haynes | Todd Jones | 764 | 700 | 64 |
| 1999-09-06 | vs DET | 138 | L 7-9 | 67-71 | 4 | 30,541 | Omar Olivares | Jeff Weaver | Dave Borkowski | Omar Olivares | Todd Jones | 771 | 709 | 62 |
| 1999-09-07 | vs BOS | 139 | L 3-5 | 67-72 | 3 | 21,195 | Gil Heredia | Tim Wakefield | Tim Wakefield | Gil Heredia | Derek Lowe | 774 | 714 | 60 |
| 1999-09-08 | vs BOS | 140 | W 6-2 | 68-72 | 3 | 20,251 | Kevin Appier | Pat Rapp | Kevin Appier | Pat Rapp | | 780 | 716 | 64 |
| 1999-09-10 | @ TBA | 141 | W 7-2 | 69-72 | 3 | 16,182 | Tim Hudson | Wilson Alvarez | Tim Hudson | Wilson Alvarez | | 787 | 718 | 69 |
| 1999-09-11 | @ TBA | 142 | W 5-4 | 70-72 | 3 | 25,362 | Omar Olivares | Ryan Rupe | Omar Olivares | Ryan Rupe | Doug Jones | 792 | 722 | 70 |
| 1999-09-12 | @ TBA | 143 | W 4-3 | 71-72 | 3 | 25,147 | Gil Heredia | Dan Wheeler | Gil Heredia | Dan Wheeler | Jason Isringhausen | 796 | 725 | 71 |
| 1999-09-13 | @ TBA | 144 | W 8-3 | 72-72 | 3 | 14,936 | Kevin Appier | Bobby Witt | Kevin Appier | Bobby Witt | | 804 | 728 | 76 |
| 1999-09-14 | @ BAL | 145 | L 6-13 | 73-72 | 3 | 40,789 | Mike Oquist | Mike Mussina | Mike Mussina | Mike Oquist | | 810 | 741 | 69 |
| 1999-09-17 | vs KCA | 146 | L 3-9 | 73-73 | 3 | 9,492 | Tim Hudson | Jay Witasick | Jay Witasick | Tim Hudson | | 813 | 750 | 63 |
| 1999-09-18 | vs KCA | 147 | W 8-4 | 74-73 | 3 | 13,651 | Omar Olivares | Jose Rosado | Omar Olivares | Jose Rosado | Jason Isringhausen | 821 | 754 | 67 |
| 1999-09-19 | vs KCA | 148 | W 12-3 | 74-74 | 3 | 13,914 | Gil Heredia | Mac Suzuki | Gil Heredia | Chris Fussell | | 833 | 757 | 76 |
| 1999-09-20 | vs MIN | 149 | L 0-4 | 74-75 | 3 | 6,512 | Kevin Appier | Jason Ryan | Jason Ryan | Kevin Appier | | 833 | 761 | 72 |
| 1999-09-21 | vs MIN | 150 | W 5-3 | 75-75 | 3 | 6,498 | Mike Oquist | Brad Radke | Ron Mahay | Hector Carrasco | Jason Isringhausen | 838 | 764 | 74 |
| 1999-09-22 | vs MIN | 151 | L 4-5 | 75-76 | 3 | 9,895 | Tim Hudson | Eric Milton | Mark Redman | Tim Worrell | Mike Trombley | 842 | 769 | 73 |
| 1999-09-23 | @ BAL | 152 | W 9-6 | 76-76 | 4 | 0 | Brett Laxton | Sidney Ponson | T.J. Mathews | Gabe Molina | Jason Isringhausen | 851 | 775 | 76 |
| 1999-09-23 | @ BAL | 153 | L 4-12 | 76-76 | 4 | 43,778 | Omar Olivares | Matt Riley | Doug Johns | Omar Olivares | | 855 | 787 | 68 |
| 1999-09-24 | @ TEX | 154 | L 4-12 | 78-76 | 3 | 40,207 | Gil Heredia | Aaron Sele | Aaron Sele | Gil Heredia | | 859 | 799 | 60 |
| 1999-09-25 | @ TEX | 155 | L 4-10 | 79-76 | 3 | 46,178 | Kevin Appier | John Burkett | John Burkett | Kevin Appier | | 863 | 809 | 54 |
| 1999-09-26 | @ TEX | 156 | L 3-10 | 80-76 | 3 | 38,656 | Kevin Jarvis | Esteban Loaiza | Esteban Loaiza | Kevin Jarvis | | 866 | 819 | 47 |
| 1999-09-28 | @ ANA | 157 | W 9-3 | 81-76 | 3 | 17,981 | Tim Hudson | Jarrod Washburn | Tim Hudson | Jarrod Washburn | Ron Mahay | 875 | 822 | 53 |
| 1999-09-29 | @ ANA | 158 | L 4-7 | 81-77 | 3 | 17,596 | Omar Olivares | Brian Cooper | Shigetoshi Hasegawa | T.J. Mathews | Lou Pote | 879 | 829 | 50 |
| 1999-09-30 | @ ANA | 159 | L 4-5 | 81-78 | 3 | 19,567 | Gil Heredia | Chuck Finley | Mark Petkovsek | Jason Isringhausen | Lou Pote | 883 | 834 | 49 |
| 1999-10-01 | vs SEA | 160 | W 5-1 | 82-78 | 3 | 14,414 | Kevin Appier | Robert Ramsay | Kevin Appier | Robert Ramsay | Doug Jones | 888 | 835 | 53 |
| 1999-10-02 | vs SEA | 161 | L 2-10 | 83-78 | 3 | 24,054 | Brett Laxton | Freddy Garcia | Freddy Garcia | Brett Laxton | | 890 | 845 | 45 |
| 1999-10-03 | vs SEA | 162 | W 3-1 | 84-78 | 3 | 25,400 | Ron Mahay | John Halama | Ron Mahay | John Halama | Jason Isringhausen | 893 | 846 | 47 |