| 1999-04-06 | @ HOU | 1 | L 2-4 | 0-1 | 5 | 51,668 | Steve Trachsel | Shane Reynolds | Shane Reynolds | Steve Trachsel | Billy Wagner | 2 | 4 | -2 |
| 1999-04-07 | @ HOU | 2 | W 9-2 | 1-1 | 2 | 23,381 | Kevin Tapani | Mike Hampton | Kevin Tapani | Mike Hampton | | 11 | 6 | 5 |
| 1999-04-08 | @ HOU | 3 | W 2-1 | 2-1 | 2 | 23,815 | Jon Lieber | Jose Lima | Jon Lieber | Jose Lima | Rod Beck | 13 | 7 | 6 |
| 1999-04-09 | @ PIT | 4 | L 1-2 | 2-2 | 2 | 19,721 | Scott Sanders | Kris Benson | Kris Benson | Scott Sanders | Mike Williams | 14 | 9 | 5 |
| 1999-04-10 | @ PIT | 5 | L 3-9 | 2-3 | 3 | 22,479 | Brad Woodall | Francisco Cordova | Scott Sauerbeck | Brad Woodall | | 17 | 18 | -1 |
| 1999-04-11 | @ PIT | 6 | L 6-9 | 2-4 | 5 | 19,384 | Steve Trachsel | Jason Schmidt | Jason Schmidt | Steve Trachsel | | 23 | 27 | -4 |
| 1999-04-12 | vs CIN | 7 | L 2-7 | 2-5 | 5 | 39,092 | Kevin Tapani | Steve Avery | Steve Avery | Kevin Tapani | | 25 | 34 | -9 |
| 1999-04-14 | vs CIN | 8 | W 5-4 | 3-5 | 5 | 23,788 | Jon Lieber | Pete Harnisch | Jon Lieber | Pete Harnisch | Rod Beck | 30 | 38 | -8 |
| 1999-04-16 | @ MIL | 9 | W 9-4 | 4-5 | 4 | 55,770 | Scott Sanders | Bill Pulsipher | Felix Heredia | Bill Pulsipher | | 39 | 42 | -3 |
| 1999-04-17 | @ MIL | 10 | L 4-5 | 4-6 | 5 | 33,479 | Steve Trachsel | Rafael Roque | Mike Myers | Rod Beck | | 43 | 47 | -4 |
| 1999-04-18 | @ MIL | 11 | W 6-5 | 5-6 | 4 | 17,847 | Brad Woodall | Steve Woodard | Rod Beck | Valerio de los Santos | Dan Serafini | 49 | 52 | -3 |
| 1999-04-20 | vs HOU | 12 | L 4-10 | 6-6 | 3 | 28,876 | Jon Lieber | Jose Lima | Jose Lima | Jon Lieber | Scott Elarton | 53 | 62 | -9 |
| 1999-04-21 | vs HOU | 13 | L 3-10 | 7-6 | 3 | 17,999 | Scott Sanders | Shane Reynolds | Shane Reynolds | Scott Sanders | | 56 | 72 | -16 |
| 1999-04-23 | vs NYN | 14 | L 5-6 | 7-7 | 3 | 20,828 | Steve Trachsel | Bobby Jones | Dennis Cook | Rod Beck | John Franco | 61 | 78 | -17 |
| 1999-04-24 | vs NYN | 15 | W 2-0 | 8-7 | 2 | 38,516 | Terry Mulholland | Allen Watson | Terry Mulholland | Allen Watson | Rod Beck | 63 | 78 | -15 |
| 1999-04-25 | vs NYN | 16 | W 8-4 | 9-7 | 2 | 39,265 | Brad Woodall | Orel Hershiser | Rodney Myers | Orel Hershiser | | 71 | 82 | -11 |
| 1999-04-27 | @ FLO | 17 | L 0-8 | 9-8 | 2 | 14,596 | Scott Sanders | Alex Fernandez | Brian Edmondson | Scott Sanders | | 71 | 90 | -19 |
| 1999-04-28 | @ FLO | 18 | W 6-1 | 10-8 | 2 | 14,312 | Steve Trachsel | Livan Hernandez | Steve Trachsel | Livan Hernandez | | 77 | 91 | -14 |
| 1999-04-29 | @ FLO | 19 | W 5-2 | 11-8 | 2 | 12,484 | Kyle Farnsworth | Jesus Sanchez | Kyle Farnsworth | Jesus Sanchez | Rod Beck | 82 | 93 | -11 |
| 1999-04-30 | vs SDN | 20 | W 6-5 | 12-8 | 1 | 24,187 | Terry Mulholland | Stan Spencer | Terry Mulholland | Stan Spencer | Rod Beck | 88 | 98 | -10 |
| 1999-05-01 | vs SDN | 21 | W 2-1 | 13-8 | 1 | 38,956 | Kevin Tapani | Matt Clement | Kevin Tapani | Matt Clement | Felix Heredia | 90 | 99 | -9 |
| 1999-05-02 | vs SDN | 22 | W 3-2 | 14-8 | 1 | 38,486 | Scott Sanders | Andy Ashby | Rodney Myers | Roberto Rivera | Rod Beck | 93 | 101 | -8 |
| 1999-05-03 | vs COL | 23 | L 1-6 | 14-9 | 1 | 32,085 | Steve Trachsel | Brian Bohanon | Brian Bohanon | Steve Trachsel | | 94 | 107 | -13 |
| 1999-05-04 | vs COL | 24 | W 13-12 | 15-9 | 1 | 28,888 | Kyle Farnsworth | Darryl Kile | Rod Beck | Jerry DiPoto | | 107 | 119 | -12 |
| 1999-05-05 | vs COL | 25 | L 6-13 | 16-9 | 1 | 30,079 | Terry Mulholland | Pedro Astacio | Pedro Astacio | Terry Mulholland | | 113 | 132 | -19 |
| 1999-05-07 | @ CIN | 26 | L 2-3 | 16-10 | 1 | 26,533 | Kevin Tapani | Pete Harnisch | Danny Graves | Rod Beck | | 115 | 135 | -20 |
| 1999-05-08 | @ CIN | 27 | W 7-4 | 17-10 | 1 | 28,993 | Jon Lieber | Denny Neagle | Jon Lieber | Denny Neagle | Rod Beck | 122 | 139 | -17 |
| 1999-05-09 | @ CIN | 28 | L 5-8 | 17-11 | 1 | 23,940 | Scott Sanders | Jason Bere | Scott Williamson | Terry Adams | Danny Graves | 127 | 147 | -20 |
| 1999-05-10 | @ LAN | 29 | L 3-4 | 17-12 | 2 | 32,925 | Steve Trachsel | Ismael Valdez | Ismael Valdez | Steve Trachsel | Jeff Shaw | 130 | 151 | -21 |
| 1999-05-11 | @ LAN | 30 | W 10-5 | 17-13 | 2 | 30,470 | Kyle Farnsworth | Carlos Perez | Kyle Farnsworth | Carlos Perez | | 140 | 156 | -16 |
| 1999-05-12 | @ LAN | 31 | L 2-3 | 17-14 | 3 | 40,007 | Kevin Tapani | Darren Dreifort | Jamie Arnold | Rod Beck | | 142 | 159 | -17 |
| 1999-05-14 | vs ATL | 32 | W 9-0 | 18-14 | 2 | 40,046 | Jon Lieber | Tom Glavine | Jon Lieber | Tom Glavine | | 151 | 159 | -8 |
| 1999-05-15 | vs ATL | 33 | W 5-1 | 19-14 | 1 | 40,332 | Steve Trachsel | Greg Maddux | Steve Trachsel | Greg Maddux | | 156 | 160 | -4 |
| 1999-05-16 | vs ATL | 34 | L 5-8 | 19-15 | 2 | 39,915 | Kyle Farnsworth | John Smoltz | Kevin McGlinchy | Rodney Myers | John Rocker | 161 | 168 | -7 |
| 1999-05-17 | @ FLO | 35 | W 8-1 | 20-15 | 2 | 13,113 | Kevin Tapani | Ryan Dempster | Kevin Tapani | Ryan Dempster | | 169 | 169 | 0 |
| 1999-05-18 | @ FLO | 36 | W 4-1 | 21-15 | 2 | 13,504 | Terry Mulholland | Alex Fernandez | Felix Heredia | Dennis Springer | Scott Sanders | 173 | 170 | 3 |
| 1999-05-19 | @ FLO | 37 | W 8-7 | 22-15 | 1 | 15,059 | Jon Lieber | Jesus Sanchez | Rodney Myers | Matt Mantei | Terry Adams | 181 | 177 | 4 |
| 1999-05-20 | @ ATL | 38 | W 6-5 | 23-15 | 1 | 38,588 | Steve Trachsel | Greg Maddux | Dan Serafini | Kevin McGlinchy | | 187 | 182 | 5 |
| 1999-05-21 | @ ATL | 39 | W 8-4 | 24-15 | 1 | 48,315 | Kyle Farnsworth | Bruce Chen | Terry Adams | Kevin McGlinchy | | 195 | 186 | 9 |
| 1999-05-22 | @ ATL | 40 | L 2-4 | 24-16 | 1 | 49,077 | Kevin Tapani | Kevin Millwood | Kevin Millwood | Kevin Tapani | John Rocker | 197 | 190 | 7 |
| 1999-05-23 | @ ATL | 41 | W 5-1 | 25-16 | 1 | 48,782 | Terry Mulholland | Odalis Perez | Terry Mulholland | Odalis Perez | | 202 | 191 | 11 |
| 1999-05-24 | vs FLO | 42 | L 5-7 | 25-17 | 1 | 31,987 | Jon Lieber | Jesus Sanchez | Matt Mantei | Rick Aguilera | | 207 | 198 | 9 |
| 1999-05-25 | vs FLO | 43 | L 3-6 | 25-18 | 1 | 35,141 | Steve Trachsel | Brian Meadows | Brian Meadows | Steve Trachsel | | 210 | 204 | 6 |
| 1999-05-26 | vs FLO | 44 | W 6-4 | 26-18 | 1 | 38,708 | Kyle Farnsworth | Livan Hernandez | Rick Aguilera | Braden Looper | | 216 | 208 | 8 |
| 1999-05-28 | vs SLN | 45 | W 6-3 | 27-18 | 1 | 39,287 | Kevin Tapani | Lance Painter | Kevin Tapani | Lance Painter | Rick Aguilera | 222 | 211 | 11 |
| 1999-05-29 | vs SLN | 46 | W 4-3 | 28-18 | 1 | 40,478 | Terry Mulholland | Darren Oliver | Felix Heredia | Ricky Bottalico | | 226 | 214 | 12 |
| 1999-05-30 | vs SLN | 47 | W 7-4 | 29-18 | 1 | 40,425 | Jon Lieber | Jose Jimenez | Jon Lieber | Jose Jimenez | | 233 | 218 | 15 |
| 1999-06-01 | vs SDN | 48 | L 0-1 | 29-19 | 1 | 34,344 | Steve Trachsel | Andy Ashby | Andy Ashby | Steve Trachsel | | 233 | 219 | 14 |
| 1999-06-02 | vs SDN | 49 | W 9-8 | 30-19 | 1 | 28,742 | Kyle Farnsworth | Heath Murray | Scott Sanders | Trevor Hoffman | | 242 | 227 | 15 |
| 1999-06-03 | vs SDN | 50 | W 7-2 | 31-19 | 1 | 33,920 | Kevin Tapani | Matt Clement | Kevin Tapani | Matt Clement | | 249 | 229 | 20 |
| 1999-06-04 | @ CLE | 51 | W 5-4 | 32-19 | 1 | 43,011 | Terry Mulholland | Bartolo Colon | Rick Aguilera | Michael Jackson | Terry Adams | 254 | 233 | 21 |
| 1999-06-05 | @ CLE | 52 | L 7-8 | 32-20 | 1 | 43,085 | Jon Lieber | Dwight Gooden | Michael Jackson | Scott Sanders | | 261 | 241 | 20 |
| 1999-06-06 | @ CLE | 53 | L 2-4 | 32-21 | 1 | 43,010 | Steve Trachsel | Charles Nagy | Charles Nagy | Steve Trachsel | Paul Shuey | 263 | 245 | 18 |
| 1999-06-07 | @ ARI | 54 | W 7-6 | 33-21 | 1 | 44,083 | Kyle Farnsworth | Brian Anderson | Terry Adams | Darren Holmes | | 270 | 251 | 19 |
| 1999-06-08 | @ ARI | 55 | W 5-3 | 34-21 | 1 | 39,308 | Kevin Tapani | Omar Daal | Rick Aguilera | Gregg Olson | Terry Adams | 275 | 254 | 21 |
| 1999-06-09 | @ ARI | 56 | L 7-8 | 34-22 | 1 | 46,033 | Terry Mulholland | Randy Johnson | Randy Johnson | Terry Mulholland | Vladimir Nunez | 282 | 262 | 20 |
| 1999-06-11 | vs CHA | 57 | L 3-5 | 34-23 | 1 | 38,989 | Jon Lieber | Jim Parque | Jim Parque | Jon Lieber | | 285 | 267 | 18 |
| 1999-06-12 | vs CHA | 58 | L 2-8 | 34-24 | 1 | 38,146 | Steve Trachsel | Mike Sirotka | Mike Sirotka | Steve Trachsel | | 287 | 275 | 12 |
| 1999-06-13 | vs CHA | 59 | L 4-6 | 34-25 | 1 | 38,071 | Kevin Tapani | Jaime Navarro | Bill Simas | Rick Aguilera | Keith Foulke | 291 | 281 | 10 |
| 1999-06-14 | @ MIL | 60 | L 1-5 | 34-26 | 1 | 41,872 | Kyle Farnsworth | Steve Woodard | Steve Woodard | Kyle Farnsworth | | 292 | 286 | 6 |
| 1999-06-15 | @ MIL | 61 | W 7-4 | 35-26 | 1 | 40,878 | Jon Lieber | Jim Abbott | Jon Lieber | Jim Abbott | Terry Adams | 299 | 290 | 9 |
| 1999-06-16 | @ MIL | 62 | L 4-11 | 36-26 | 1 | 39,891 | Steve Trachsel | Hideo Nomo | Hideo Nomo | Steve Trachsel | | 303 | 301 | 2 |
| 1999-06-17 | @ SFN | 63 | L 2-3 | 36-27 | 1 | 18,886 | Terry Mulholland | Kirk Rueter | Robb Nen | Dan Serafini | | 305 | 304 | 1 |
| 1999-06-18 | @ SFN | 64 | L 5-8 | 36-28 | 1 | 22,357 | Kevin Tapani | Russ Ortiz | Russ Ortiz | Kevin Tapani | Robb Nen | 310 | 312 | -2 |
| 1999-06-19 | @ SFN | 65 | L 5-11 | 37-28 | 1 | 36,550 | Kyle Farnsworth | Shawn Estes | Shawn Estes | Kyle Farnsworth | | 315 | 323 | -8 |
| 1999-06-20 | @ SFN | 66 | L 6-7 | 37-29 | 1 | 53,245 | Jon Lieber | Chris Brock | Alan Embree | Rick Aguilera | | 321 | 330 | -9 |
| 1999-06-22 | @ COL | 67 | W 13-12 | 38-29 | 1 | 48,081 | Steve Trachsel | Darryl Kile | Scott Sanders | Mike DeJean | Rick Aguilera | 334 | 342 | -8 |
| 1999-06-23 | @ COL | 68 | L 1-10 | 38-30 | 1 | 48,189 | Terry Mulholland | Pedro Astacio | Pedro Astacio | Terry Mulholland | | 335 | 352 | -17 |
| 1999-06-24 | @ COL | 69 | W 12-10 | 39-30 | 1 | 48,876 | Kevin Tapani | Bobby Jones | Kevin Tapani | Bobby Jones | | 347 | 362 | -15 |
| 1999-06-25 | vs PHI | 70 | L 2-3 | 39-31 | 1 | 40,553 | Jon Lieber | Chad Ogea | Chad Ogea | Jon Lieber | Wayne Gomes | 349 | 365 | -16 |
| 1999-06-26 | vs PHI | 71 | L 2-6 | 39-32 | 1 | 40,466 | Steve Trachsel | Robert Person | Robert Person | Steve Trachsel | | 351 | 371 | -20 |
| 1999-06-27 | vs PHI | 72 | W 13-7 | 39-33 | 2 | 38,455 | Terry Mulholland | Randy Wolf | Terry Mulholland | Mike Grace | | 364 | 378 | -14 |
| 1999-06-29 | vs MIL | 73 | L 6-17 | 40-33 | 2 | 40,415 | Kevin Tapani | Steve Woodard | Steve Woodard | Kevin Tapani | | 370 | 395 | -25 |
| 1999-06-30 | vs MIL | 74 | W 5-4 | 41-33 | 2 | 38,898 | Jon Lieber | Jim Abbott | Matt Karchner | David Weathers | Rick Aguilera | 375 | 399 | -24 |
| 1999-07-01 | vs MIL | 75 | L 12-19 | 41-34 | 2 | 39,561 | Steve Trachsel | Hideo Nomo | Mike Myers | Steve Trachsel | | 387 | 418 | -31 |
| 1999-07-02 | @ PHI | 76 | L 1-14 | 41-35 | 2 | 50,498 | Terry Mulholland | Randy Wolf | Randy Wolf | Terry Mulholland | | 388 | 432 | -44 |
| 1999-07-03 | @ PHI | 77 | L 8-21 | 42-35 | 2 | 58,086 | Kyle Farnsworth | Paul Byrd | Paul Byrd | Kyle Farnsworth | | 396 | 453 | -57 |
| 1999-07-04 | @ PHI | 78 | L 2-6 | 42-36 | 2 | 20,097 | Kevin Tapani | Curt Schilling | Curt Schilling | Kevin Tapani | | 398 | 459 | -61 |
| 1999-07-05 | @ PIT | 79 | W 5-2 | 43-36 | 2 | 19,762 | Jon Lieber | Jason Schmidt | Jon Lieber | Jason Schmidt | Rick Aguilera | 403 | 461 | -58 |
| 1999-07-06 | @ PIT | 80 | L 1-6 | 43-37 | 3 | 14,367 | Steve Trachsel | Todd Ritchie | Todd Ritchie | Steve Trachsel | | 404 | 467 | -63 |
| 1999-07-07 | @ PIT | 81 | L 1-4 | 43-38 | 3 | 28,258 | Terry Mulholland | Francisco Cordova | Francisco Cordova | Terry Mulholland | | 405 | 471 | -66 |
| 1999-07-08 | @ PIT | 82 | W 9-4 | 44-38 | 3 | 17,711 | Dan Serafini | Kris Benson | Dan Serafini | Kris Benson | Scott Sanders | 414 | 475 | -61 |
| 1999-07-09 | @ CHA | 83 | L 2-3 | 44-39 | 3 | 44,153 | Kevin Tapani | Mike Sirotka | Bob Howry | Terry Adams | | 416 | 478 | -62 |
| 1999-07-10 | @ CHA | 84 | W 10-2 | 44-40 | 4 | 44,008 | Jon Lieber | Jaime Navarro | Jon Lieber | Jaime Navarro | | 426 | 480 | -54 |
| 1999-07-11 | @ CHA | 85 | W 6-3 | 45-40 | 4 | 43,115 | Steve Trachsel | James Baldwin | Steve Trachsel | James Baldwin | Terry Adams | 432 | 483 | -51 |
| 1999-07-15 | vs MIN | 86 | W 9-3 | 46-40 | 4 | 39,420 | Dan Serafini | Brad Radke | Scott Sanders | Brad Radke | Terry Adams | 441 | 486 | -45 |
| 1999-07-16 | vs MIN | 87 | W 11-10 | 47-40 | 3 | 39,249 | Jon Lieber | Eric Milton | Terry Adams | Mike Trombley | | 452 | 496 | -44 |
| 1999-07-17 | vs MIN | 88 | L 0-8 | 47-41 | 4 | 39,044 | Terry Mulholland | Joe Mays | Joe Mays | Terry Mulholland | | 452 | 504 | -52 |
| 1999-07-18 | vs KCA | 89 | L 4-5 | 47-42 | 4 | 38,655 | Kevin Tapani | Jeff Suppan | Jeff Suppan | Kevin Tapani | Scott Service | 456 | 509 | -53 |
| 1999-07-19 | vs KCA | 90 | L 2-10 | 48-42 | 4 | 38,725 | Steve Trachsel | Jay Witasick | Jay Witasick | Steve Trachsel | | 458 | 519 | -61 |
| 1999-07-20 | vs KCA | 91 | W 8-7 | 49-42 | 3 | 39,081 | Dan Serafini | Dan Reichert | Scott Sanders | Brian Barber | Terry Adams | 466 | 526 | -60 |
| 1999-07-21 | vs PIT | 92 | W 2-1 | 50-42 | 3 | 37,006 | Jon Lieber | Francisco Cordova | Rick Aguilera | Jason Christiansen | | 468 | 527 | -59 |
| 1999-07-22 | vs PIT | 93 | W 5-3 | 51-42 | 1 | 37,112 | Terry Mulholland | Kris Benson | Terry Mulholland | Kris Benson | Terry Adams | 473 | 530 | -57 |
| 1999-07-23 | @ NYN | 94 | L 4-5 | 51-43 | 2 | 52,135 | Kevin Tapani | Masato Yoshii | Dennis Cook | Kevin Tapani | Armando Benitez | 477 | 535 | -58 |
| 1999-07-24 | @ NYN | 95 | L 1-2 | 51-44 | 3 | 47,995 | Steve Trachsel | Octavio Dotel | Octavio Dotel | Steve Trachsel | Armando Benitez | 478 | 537 | -59 |
| 1999-07-25 | @ NYN | 96 | L 1-5 | 51-45 | 4 | 47,679 | Dan Serafini | Al Leiter | Al Leiter | Dan Serafini | | 479 | 542 | -63 |
| 1999-07-26 | @ MON | 97 | L 1-6 | 51-46 | 4 | 10,544 | Jon Lieber | Dan Smith | Dan Smith | Jon Lieber | | 480 | 548 | -68 |
| 1999-07-27 | @ MON | 98 | W 4-2 | 52-46 | 4 | 10,667 | Terry Mulholland | Dustin Hermanson | Terry Mulholland | Dustin Hermanson | Terry Adams | 484 | 550 | -66 |
| 1999-07-28 | @ MON | 99 | L 2-8 | 52-47 | 4 | 9,608 | Kevin Tapani | Javier Vazquez | Javier Vazquez | Kevin Tapani | | 486 | 558 | -72 |
| 1999-07-30 | vs NYN | 100 | L 9-10 | 53-47 | 4 | 38,594 | Steve Trachsel | Masato Yoshii | Pat Mahomes | Kyle Farnsworth | Armando Benitez | 495 | 568 | -73 |
| 1999-07-31 | vs NYN | 101 | W 17-10 | 54-47 | 4 | 39,431 | Jon Lieber | Octavio Dotel | Dan Serafini | Jason Isringhausen | | 512 | 578 | -66 |
| 1999-08-01 | vs NYN | 102 | L 4-5 | 54-48 | 4 | 39,222 | Kyle Farnsworth | Al Leiter | Pat Mahomes | Scott Sanders | | 516 | 583 | -67 |
| 1999-08-02 | vs MON | 103 | L 1-5 | 54-49 | 4 | 37,598 | Kevin Tapani | Dustin Hermanson | Dustin Hermanson | Kevin Tapani | Ugueth Urbina | 517 | 588 | -71 |
| 1999-08-03 | vs MON | 104 | L 4-9 | 54-50 | 4 | 37,909 | Micah Bowie | Javier Vazquez | Javier Vazquez | Micah Bowie | | 521 | 597 | -76 |
| 1999-08-04 | vs MON | 105 | W 5-1 | 55-50 | 4 | 33,465 | Steve Trachsel | Jeremy Powell | Steve Trachsel | Jeremy Powell | | 526 | 598 | -72 |
| 1999-08-05 | vs MON | 106 | L 2-5 | 55-51 | 4 | 38,857 | Jon Lieber | Mike Thurman | Mike Thurman | Jon Lieber | Ugueth Urbina | 528 | 603 | -75 |
| 1999-08-06 | vs HOU | 107 | L 1-6 | 55-52 | 7 | 0 | Kyle Farnsworth | Jose Lima | Jose Lima | Kyle Farnsworth | Jay Powell | 529 | 609 | -80 |
| 1999-08-06 | vs HOU | 108 | W 6-0 | 55-52 | 7 | 39,109 | Andrew Lorraine | Sean Bergman | Andrew Lorraine | Sean Bergman | | 535 | 609 | -74 |
| 1999-08-07 | vs HOU | 109 | L 4-10 | 57-52 | 4 | 38,413 | Kevin Tapani | Scott Elarton | Scott Elarton | Kevin Tapani | | 539 | 619 | -80 |
| 1999-08-08 | vs HOU | 110 | L 2-6 | 57-53 | 4 | 38,296 | Micah Bowie | Mike Hampton | Mike Hampton | Micah Bowie | | 541 | 625 | -84 |
| 1999-08-09 | vs ARI | 111 | L 7-10 | 58-53 | 4 | 38,679 | Steve Trachsel | Omar Daal | Omar Daal | Scott Sanders | | 548 | 635 | -87 |
| 1999-08-10 | vs ARI | 112 | L 1-3 | 58-54 | 4 | 32,787 | Jon Lieber | Brian Anderson | Greg Swindell | Jon Lieber | Gregg Olson | 549 | 638 | -89 |
| 1999-08-11 | vs ARI | 113 | L 5-7 | 58-55 | 4 | 39,334 | Andrew Lorraine | Randy Johnson | Dan Plesac | Steve Rain | Gregg Olson | 554 | 645 | -91 |
| 1999-08-13 | @ SLN | 114 | L 1-7 | 58-56 | 4 | 48,628 | Kyle Farnsworth | Kent Bottenfield | Kent Bottenfield | Kyle Farnsworth | | 555 | 652 | -97 |
| 1999-08-14 | @ SLN | 115 | W 9-7 | 59-56 | 4 | 48,615 | Micah Bowie | Darren Oliver | Terry Adams | Heathcliff Slocumb | | 564 | 659 | -95 |
| 1999-08-15 | @ SLN | 116 | L 5-6 | 59-57 | 4 | 48,392 | Steve Trachsel | Jose Jimenez | Ricky Bottalico | Terry Adams | | 569 | 665 | -96 |
| 1999-08-16 | @ ARI | 117 | L 3-10 | 60-57 | 4 | 42,225 | Jon Lieber | Randy Johnson | Randy Johnson | Jon Lieber | | 572 | 675 | -103 |
| 1999-08-17 | @ ARI | 118 | L 0-4 | 60-58 | 4 | 39,403 | Andrew Lorraine | Brian Anderson | Brian Anderson | Andrew Lorraine | | 572 | 679 | -107 |
| 1999-08-18 | @ ARI | 119 | L 1-3 | 60-59 | 4 | 41,571 | Kevin Tapani | Andy Benes | Andy Benes | Kevin Tapani | Matt Mantei | 573 | 682 | -109 |
| 1999-08-20 | vs COL | 120 | L 3-11 | 61-59 | 4 | 40,130 | Kyle Farnsworth | Pedro Astacio | Pedro Astacio | Kyle Farnsworth | | 576 | 693 | -117 |
| 1999-08-21 | vs COL | 121 | W 8-6 | 62-59 | 4 | 40,087 | Micah Bowie | John Thomson | Micah Bowie | John Thomson | Terry Adams | 584 | 699 | -115 |
| 1999-08-22 | vs COL | 122 | L 2-3 | 62-60 | 5 | 38,424 | Steve Trachsel | Jamey Wright | Jamey Wright | Steve Trachsel | Dave Veres | 586 | 702 | -116 |
| 1999-08-24 | vs SFN | 123 | L 4-12 | 63-60 | 4 | 25,501 | Andrew Lorraine | Shawn Estes | Shawn Estes | Andrew Lorraine | | 590 | 714 | -124 |
| 1999-08-25 | vs SFN | 124 | L 5-11 | 64-61 | 5 | 0 | Kevin Tapani | Russ Ortiz | Russ Ortiz | Kevin Tapani | | 595 | 725 | -130 |
| 1999-08-25 | vs SFN | 125 | L 5-6 | 64-61 | 5 | 26,584 | Jon Lieber | Kirk Rueter | Kirk Rueter | Jon Lieber | Robb Nen | 600 | 731 | -131 |
| 1999-08-26 | vs SFN | 126 | W 11-10 | 65-61 | 4 | 28,351 | Micah Bowie | Livan Hernandez | Terry Adams | Robb Nen | | 611 | 741 | -130 |
| 1999-08-27 | @ LAN | 127 | L 0-9 | 65-62 | 5 | 44,230 | Steve Trachsel | Ismael Valdez | Ismael Valdez | Steve Trachsel | | 611 | 750 | -139 |
| 1999-08-28 | @ LAN | 128 | L 3-4 | 65-63 | 4 | 46,129 | Andrew Lorraine | Chan Ho Park | Chan Ho Park | Andrew Lorraine | Jeff Shaw | 614 | 754 | -140 |
| 1999-08-29 | @ LAN | 129 | W 6-0 | 66-63 | 4 | 47,411 | Kyle Farnsworth | Darren Dreifort | Kyle Farnsworth | Darren Dreifort | | 620 | 754 | -134 |
| 1999-08-30 | @ SDN | 130 | L 4-8 | 66-64 | 4 | 21,874 | Jon Lieber | Matt Clement | Donne Wall | Felix Heredia | | 624 | 762 | -138 |
| 1999-08-31 | @ SDN | 131 | L 3-7 | 66-65 | 4 | 24,935 | Micah Bowie | Andy Ashby | Andy Ashby | Micah Bowie | | 627 | 769 | -142 |
| 1999-09-01 | @ SDN | 132 | W 1-0 | 67-65 | 4 | 31,132 | Steve Trachsel | Sterling Hitchcock | Steve Trachsel | Sterling Hitchcock | Terry Adams | 628 | 769 | -141 |
| 1999-09-03 | vs LAN | 133 | L 6-8 | 67-66 | 4 | 28,435 | Andrew Lorraine | Chan Ho Park | Chan Ho Park | Scott Sanders | Jeff Shaw | 634 | 777 | -143 |
| 1999-09-04 | vs LAN | 134 | L 0-6 | 67-67 | 4 | 39,048 | Kyle Farnsworth | Kevin Brown | Kevin Brown | Kyle Farnsworth | | 634 | 783 | -149 |
| 1999-09-05 | vs LAN | 135 | L 1-4 | 67-68 | 4 | 39,921 | Jon Lieber | Darren Dreifort | Darren Dreifort | Jon Lieber | Jeff Shaw | 635 | 787 | -152 |
| 1999-09-06 | vs CIN | 136 | L 3-6 | 67-69 | 4 | 35,832 | Micah Bowie | Juan Guzman | Juan Guzman | Micah Bowie | Danny Graves | 638 | 793 | -155 |
| 1999-09-07 | vs CIN | 137 | W 2-1 | 68-69 | 6 | 0 | Steve Trachsel | Ron Villone | Steve Trachsel | Ron Villone | Terry Adams | 640 | 794 | -154 |
| 1999-09-07 | vs CIN | 138 | L 3-10 | 68-69 | 6 | 33,040 | Brian McNichol | Brett Tomko | Brett Tomko | Brian McNichol | | 643 | 804 | -161 |
| 1999-09-08 | vs CIN | 139 | L 4-6 | 69-70 | 4 | 35,200 | Andrew Lorraine | Steve Parris | Steve Parris | Andrew Lorraine | Danny Graves | 647 | 810 | -163 |
| 1999-09-09 | vs CIN | 140 | L 3-5 | 69-71 | 4 | 34,976 | Kyle Farnsworth | Pete Harnisch | Scott Sullivan | Kyle Farnsworth | Danny Graves | 650 | 815 | -165 |
| 1999-09-10 | @ HOU | 141 | L 4-6 | 69-72 | 4 | 48,879 | Jon Lieber | Scott Elarton | Billy Wagner | Bobby Ayala | | 654 | 821 | -167 |
| 1999-09-11 | @ HOU | 142 | L 3-5 | 69-73 | 4 | 52,010 | Micah Bowie | Jose Lima | Jose Lima | Micah Bowie | Billy Wagner | 657 | 826 | -169 |
| 1999-09-12 | @ HOU | 143 | L 1-7 | 69-74 | 4 | 51,877 | Steve Trachsel | Chris Holt | Chris Holt | Steve Trachsel | | 658 | 833 | -175 |
| 1999-09-14 | @ CIN | 144 | W 4-3 | 70-74 | 4 | 23,352 | Kyle Farnsworth | Pete Harnisch | Kyle Farnsworth | Pete Harnisch | Terry Adams | 662 | 836 | -174 |
| 1999-09-15 | @ CIN | 145 | L 4-5 | 70-75 | 4 | 21,794 | Jon Lieber | Denny Neagle | Denny Neagle | Jon Lieber | Danny Graves | 666 | 841 | -175 |
| 1999-09-16 | @ CIN | 146 | W 7-6 | 71-75 | 4 | 23,176 | Andrew Lorraine | Juan Guzman | Terry Adams | Danny Graves | Rick Aguilera | 673 | 847 | -174 |
| 1999-09-17 | vs MIL | 147 | W 6-5 | 72-75 | 3 | 34,266 | Steve Trachsel | Steve Woodard | Rick Aguilera | Kyle Peterson | | 679 | 852 | -173 |
| 1999-09-18 | vs MIL | 148 | L 4-7 | 72-76 | 3 | 39,304 | Micah Bowie | Jason Bere | Kyle Peterson | Mark Guthrie | | 683 | 859 | -176 |
| 1999-09-19 | vs MIL | 149 | W 8-7 | 73-76 | 3 | 37,527 | Kyle Farnsworth | Hideo Nomo | Rick Aguilera | Hector Ramirez | | 691 | 866 | -175 |
| 1999-09-20 | vs SLN | 150 | L 2-7 | 73-77 | 3 | 38,085 | Jon Lieber | Mark Thompson | Mark Thompson | Jon Lieber | | 693 | 873 | -180 |
| 1999-09-21 | vs SLN | 151 | L 2-7 | 73-78 | 4 | 38,254 | Andrew Lorraine | Kent Bottenfield | Kent Bottenfield | Andrew Lorraine | | 695 | 880 | -185 |
| 1999-09-22 | vs SLN | 152 | W 5-3 | 74-78 | 3 | 38,278 | Steve Trachsel | Garrett Stephenson | Steve Trachsel | Garrett Stephenson | Rick Aguilera | 700 | 883 | -183 |
| 1999-09-23 | vs PIT | 153 | W 8-5 | 75-78 | 3 | 36,736 | Micah Bowie | Chris Peters | Micah Bowie | Chris Peters | Rick Aguilera | 708 | 888 | -180 |
| 1999-09-24 | vs PIT | 154 | W 9-0 | 76-78 | 3 | 29,267 | Kyle Farnsworth | Jason Schmidt | Kyle Farnsworth | Jason Schmidt | | 717 | 888 | -171 |
| 1999-09-25 | vs PIT | 155 | W 3-1 | 77-78 | 3 | 39,035 | Jon Lieber | Francisco Cordova | Jon Lieber | Francisco Cordova | | 720 | 889 | -169 |
| 1999-09-26 | vs PIT | 156 | L 4-8 | 77-79 | 3 | 39,663 | Andrew Lorraine | Kris Benson | Scott Sauerbeck | Mark Guthrie | | 724 | 897 | -173 |
| 1999-09-28 | @ PHI | 157 | W 8-2 | 78-79 | 3 | 16,106 | Steve Trachsel | Randy Wolf | Steve Trachsel | Randy Wolf | | 732 | 899 | -167 |
| 1999-09-29 | @ PHI | 158 | L 0-5 | 78-80 | 3 | 21,142 | Micah Bowie | Carlton Loewer | Billy Brewer | Micah Bowie | | 732 | 904 | -172 |
| 1999-09-30 | @ PHI | 159 | L 1-2 | 78-81 | 3 | 17,475 | Brian McNichol | Robert Person | Robert Person | Brian McNichol | Steve Montgomery | 733 | 906 | -173 |
| 1999-10-01 | @ SLN | 160 | W 3-2 | 79-81 | 3 | 49,085 | Jon Lieber | Mark Thompson | Jon Lieber | Mark Thompson | | 736 | 908 | -172 |
| 1999-10-02 | @ SLN | 161 | W 6-3 | 80-81 | 3 | 48,841 | Andrew Lorraine | Garrett Stephenson | Andrew Lorraine | Garrett Stephenson | Rick Aguilera | 742 | 911 | -169 |
| 1999-10-03 | @ SLN | 162 | L 5-9 | 80-82 | 3 | 47,998 | Steve Trachsel | Larry Luebbers | Larry Luebbers | Steve Trachsel | Rick Ankiel | 747 | 920 | -173 |