| 1999-04-05 | @ CIN | 1 | W 11-8 | 0-1 | 4 | 55,112 | Mark Gardner | Brett Tomko | Alan Embree | John Hudek | Robb Nen | 11 | 8 | 3 |
| 1999-04-06 | @ CIN | 2 | W 7-6 | 1-1 | 4 | 17,310 | Kirk Rueter | Jason Bere | Julian Tavarez | Danny Graves | Robb Nen | 18 | 14 | 4 |
| 1999-04-07 | @ CIN | 3 | W 8-3 | 2-1 | 3 | 19,011 | Russ Ortiz | Steve Avery | Russ Ortiz | Steve Avery | | 26 | 17 | 9 |
| 1999-04-08 | vs SDN | 4 | W 12-4 | 2-2 | 4 | 57,430 | Shawn Estes | Stan Spencer | Shawn Estes | Stan Spencer | | 38 | 21 | 17 |
| 1999-04-09 | vs SDN | 5 | W 8-3 | 3-2 | 3 | 15,795 | Chris Brock | Matt Clement | Chris Brock | Matt Clement | | 46 | 24 | 22 |
| 1999-04-10 | vs SDN | 6 | L 1-11 | 3-3 | 3 | 18,331 | Mark Gardner | Andy Ashby | Andy Ashby | Mark Gardner | | 47 | 35 | 12 |
| 1999-04-11 | vs SDN | 7 | W 8-6 | 4-3 | 3 | 22,330 | Kirk Rueter | Sterling Hitchcock | John Johnstone | Roberto Rivera | Robb Nen | 55 | 41 | 14 |
| 1999-04-13 | vs HOU | 8 | L 3-7 | 4-4 | 3 | 9,425 | Russ Ortiz | Mike Hampton | Mike Hampton | Russ Ortiz | Jay Powell | 58 | 48 | 10 |
| 1999-04-14 | vs HOU | 9 | L 3-6 | 4-5 | 3 | 11,274 | Shawn Estes | Jose Lima | Jose Lima | Shawn Estes | Billy Wagner | 61 | 54 | 7 |
| 1999-04-15 | vs HOU | 10 | W 5-2 | 5-5 | 3 | 10,819 | Chris Brock | Sean Bergman | Chris Brock | Sean Bergman | Robb Nen | 66 | 56 | 10 |
| 1999-04-16 | @ ARI | 11 | L 4-10 | 6-5 | 3 | 34,516 | Mark Gardner | Todd Stottlemyre | Todd Stottlemyre | Mark Gardner | Brian Anderson | 70 | 66 | 4 |
| 1999-04-17 | @ ARI | 12 | W 8-5 | 7-5 | 2 | 36,674 | Kirk Rueter | Andy Benes | Kirk Rueter | Andy Benes | | 78 | 71 | 7 |
| 1999-04-18 | @ ARI | 13 | L 3-12 | 8-5 | 2 | 36,043 | Russ Ortiz | Armando Reynoso | Armando Reynoso | Russ Ortiz | | 81 | 83 | -2 |
| 1999-04-19 | vs FLO | 14 | W 5-4 | 9-5 | 2 | 10,474 | Shawn Estes | Jesus Sanchez | John Johnstone | Antonio Alfonseca | Robb Nen | 86 | 87 | -1 |
| 1999-04-20 | vs FLO | 15 | L 2-7 | 9-6 | 2 | 10,765 | Chris Brock | Brian Meadows | Brian Meadows | Chris Brock | Brian Edmondson | 88 | 94 | -6 |
| 1999-04-21 | vs FLO | 16 | W 4-0 | 10-6 | 2 | 10,249 | Joe Nathan | Dennis Springer | Joe Nathan | Dennis Springer | | 92 | 94 | -2 |
| 1999-04-22 | vs COL | 17 | L 5-8 | 10-7 | 2 | 11,061 | Kirk Rueter | Brian Bohanon | Brian Bohanon | Kirk Rueter | Dave Veres | 97 | 102 | -5 |
| 1999-04-23 | vs COL | 18 | W 7-2 | 11-7 | 2 | 16,271 | Russ Ortiz | Darryl Kile | Russ Ortiz | Darryl Kile | | 104 | 104 | 0 |
| 1999-04-24 | vs COL | 19 | W 8-4 | 12-7 | 2 | 26,626 | Shawn Estes | Pedro Astacio | Shawn Estes | Pedro Astacio | | 112 | 108 | 4 |
| 1999-04-25 | vs COL | 20 | W 7-6 | 13-7 | 2 | 23,099 | Chris Brock | Jamey Wright | Alan Embree | Mike DeJean | Robb Nen | 119 | 114 | 5 |
| 1999-04-27 | @ MON | 21 | W 3-2 | 14-7 | 2 | 5,202 | Kirk Rueter | Miguel Batista | John Johnstone | Steve Kline | Robb Nen | 122 | 116 | 6 |
| 1999-04-28 | @ MON | 22 | W 4-3 | 15-7 | 2 | 4,998 | Joe Nathan | Dustin Hermanson | Joe Nathan | Dustin Hermanson | Robb Nen | 126 | 119 | 7 |
| 1999-04-29 | @ MON | 23 | W 6-5 | 16-7 | 1 | 5,253 | Russ Ortiz | Carl Pavano | Russ Ortiz | Carl Pavano | Robb Nen | 132 | 124 | 8 |
| 1999-04-30 | @ NYN | 24 | L 2-7 | 16-8 | 2 | 32,427 | Shawn Estes | Allen Watson | Allen Watson | Shawn Estes | Turk Wendell | 134 | 131 | 3 |
| 1999-05-01 | @ NYN | 25 | L 4-9 | 16-9 | 2 | 33,825 | Chris Brock | Orel Hershiser | Orel Hershiser | Chris Brock | | 138 | 140 | -2 |
| 1999-05-02 | @ NYN | 26 | L 0-2 | 16-10 | 2 | 37,431 | Kirk Rueter | Masato Yoshii | Dennis Cook | John Johnstone | John Franco | 138 | 142 | -4 |
| 1999-05-03 | @ PIT | 27 | L 8-9 | 16-11 | 2 | 11,099 | Joe Nathan | Chris Peters | Rich Loiselle | Robb Nen | | 146 | 151 | -5 |
| 1999-05-04 | @ PIT | 28 | W 7-4 | 17-11 | 2 | 10,532 | Russ Ortiz | Jose Silva | Russ Ortiz | Jose Silva | | 153 | 155 | -2 |
| 1999-05-05 | @ PIT | 29 | L 3-4 | 17-12 | 2 | 14,358 | Shawn Estes | Pete Schourek | Rich Loiselle | Felix Rodriguez | | 156 | 159 | -3 |
| 1999-05-07 | vs MIL | 30 | W 4-3 | 18-12 | 2 | 15,650 | Chris Brock | Rafael Roque | Chris Brock | Rafael Roque | Robb Nen | 160 | 162 | -2 |
| 1999-05-08 | vs MIL | 31 | W 6-4 | 19-12 | 2 | 20,144 | Kirk Rueter | Steve Woodard | Kirk Rueter | Steve Woodard | Robb Nen | 166 | 166 | 0 |
| 1999-05-09 | vs MIL | 32 | L 2-3 | 19-13 | 2 | 35,054 | Mark Gardner | Hideo Nomo | Hideo Nomo | Mark Gardner | Bob Wickman | 168 | 169 | -1 |
| 1999-05-10 | vs ATL | 33 | W 4-1 | 20-13 | 2 | 14,694 | Russ Ortiz | John Smoltz | Russ Ortiz | John Smoltz | Robb Nen | 172 | 170 | 2 |
| 1999-05-11 | vs ATL | 34 | L 8-9 | 20-14 | 2 | 18,917 | Shawn Estes | Odalis Perez | John Rocker | Felix Rodriguez | | 180 | 179 | 1 |
| 1999-05-12 | vs ATL | 35 | W 5-1 | 21-14 | 2 | 18,550 | Chris Brock | Kevin Millwood | Chris Brock | Kevin Millwood | | 185 | 180 | 5 |
| 1999-05-14 | @ HOU | 36 | L 4-7 | 21-15 | 2 | 34,177 | Kirk Rueter | Shane Reynolds | Shane Reynolds | Kirk Rueter | Billy Wagner | 189 | 187 | 2 |
| 1999-05-15 | @ HOU | 37 | L 5-10 | 22-15 | 2 | 40,871 | Mark Gardner | Mike Hampton | Mike Hampton | Mark Gardner | | 194 | 197 | -3 |
| 1999-05-16 | @ HOU | 38 | W 5-4 | 23-15 | 2 | 29,671 | Russ Ortiz | Sean Bergman | Robb Nen | Scott Elarton | Joe Nathan | 199 | 201 | -2 |
| 1999-05-17 | vs ARI | 39 | L 1-12 | 23-16 | 2 | 10,846 | Shawn Estes | Todd Stottlemyre | John Frascatore | Shawn Estes | | 200 | 213 | -13 |
| 1999-05-18 | vs ARI | 40 | L 3-7 | 23-17 | 2 | 10,900 | Chris Brock | Armando Reynoso | Armando Reynoso | Chris Brock | | 203 | 220 | -17 |
| 1999-05-19 | vs ARI | 41 | W 8-3 | 24-17 | 2 | 15,793 | Kirk Rueter | Andy Benes | Kirk Rueter | Andy Benes | | 211 | 223 | -12 |
| 1999-05-21 | vs HOU | 42 | W 4-3 | 25-17 | 2 | 25,172 | Mark Gardner | Sean Bergman | John Johnstone | Jay Powell | Robb Nen | 215 | 226 | -11 |
| 1999-05-22 | vs HOU | 43 | W 3-1 | 26-17 | 2 | 21,942 | Russ Ortiz | Chris Holt | Russ Ortiz | Chris Holt | Robb Nen | 218 | 227 | -9 |
| 1999-05-23 | vs HOU | 44 | L 1-4 | 26-18 | 2 | 40,101 | Shawn Estes | Jose Lima | Jose Lima | Joe Nathan | Billy Wagner | 219 | 231 | -12 |
| 1999-05-25 | @ SLN | 45 | W 17-1 | 27-18 | 2 | 45,029 | Chris Brock | Jose Jimenez | Chris Brock | Jose Jimenez | | 236 | 232 | 4 |
| 1999-05-26 | @ SLN | 46 | W 7-6 | 28-18 | 2 | 36,143 | Kirk Rueter | Kent Bottenfield | Kirk Rueter | Kent Bottenfield | Robb Nen | 243 | 238 | 5 |
| 1999-05-27 | @ SLN | 47 | L 2-3 | 28-19 | 2 | 47,829 | Mark Gardner | Juan Acevedo | Heathcliff Slocumb | Jerry Spradlin | | 245 | 241 | 4 |
| 1999-05-28 | @ MON | 48 | L 2-4 | 28-20 | 2 | 6,535 | Russ Ortiz | Javier Vazquez | Anthony Telford | Russ Ortiz | Ugueth Urbina | 247 | 245 | 2 |
| 1999-05-29 | @ MON | 49 | L 4-7 | 28-21 | 2 | 8,516 | Shawn Estes | Mike Thurman | Mike Thurman | Shawn Estes | Ugueth Urbina | 251 | 252 | -1 |
| 1999-05-30 | @ MON | 50 | L 4-6 | 28-22 | 2 | 8,172 | Chris Brock | Miguel Batista | Miguel Batista | Chris Brock | Ugueth Urbina | 255 | 258 | -3 |
| 1999-05-31 | @ PHI | 51 | L 3-4 | 28-23 | 2 | 16,323 | Kirk Rueter | Carlton Loewer | Yorkis Perez | John Johnstone | Wayne Gomes | 258 | 262 | -4 |
| 1999-06-01 | @ PHI | 52 | W 6-5 | 29-23 | 2 | 13,050 | Mark Gardner | Robert Person | Robb Nen | Wayne Gomes | | 264 | 267 | -3 |
| 1999-06-02 | @ PHI | 53 | L 6-7 | 29-24 | 2 | 13,616 | Russ Ortiz | Paul Byrd | Paul Byrd | Russ Ortiz | Wayne Gomes | 270 | 274 | -4 |
| 1999-06-03 | @ PHI | 54 | W 7-4 | 30-24 | 2 | 20,560 | Shawn Estes | Curt Schilling | Jerry Spradlin | Curt Schilling | Robb Nen | 277 | 278 | -1 |
| 1999-06-04 | vs OAK | 55 | W 4-3 | 31-24 | 2 | 32,456 | Chris Brock | Gil Heredia | Jerry Spradlin | Billy Taylor | | 281 | 281 | 0 |
| 1999-06-05 | vs OAK | 56 | W 8-0 | 32-24 | 2 | 31,959 | Kirk Rueter | Mike Oquist | Kirk Rueter | Mike Oquist | | 289 | 281 | 8 |
| 1999-06-06 | vs OAK | 57 | L 6-7 | 32-25 | 2 | 40,154 | Mark Gardner | Kenny Rogers | Buddy Groom | John Johnstone | Billy Taylor | 295 | 288 | 7 |
| 1999-06-07 | vs ANA | 58 | W 5-2 | 33-25 | 2 | 13,661 | Russ Ortiz | Chuck Finley | Russ Ortiz | Chuck Finley | Robb Nen | 300 | 290 | 10 |
| 1999-06-08 | vs ANA | 59 | W 6-2 | 34-25 | 2 | 11,721 | Shawn Estes | Steve Sparks | Shawn Estes | Steve Sparks | | 306 | 292 | 14 |
| 1999-06-09 | vs ANA | 60 | L 1-2 | 34-26 | 2 | 17,516 | Chris Brock | Tim Belcher | Tim Belcher | Chris Brock | Troy Percival | 307 | 294 | 13 |
| 1999-06-11 | @ SEA | 61 | L 3-7 | 34-27 | 2 | 29,527 | Mark Gardner | Jamie Moyer | Jamie Moyer | Mark Gardner | Jose Mesa | 310 | 301 | 9 |
| 1999-06-12 | @ SEA | 62 | W 15-11 | 35-27 | 2 | 35,625 | Kirk Rueter | Freddy Garcia | Kirk Rueter | Freddy Garcia | | 325 | 312 | 13 |
| 1999-06-13 | @ SEA | 63 | W 8-4 | 36-27 | 2 | 33,500 | Russ Ortiz | John Halama | Julian Tavarez | Jose Paniagua | | 333 | 316 | 17 |
| 1999-06-14 | @ COL | 64 | L 4-5 | 36-28 | 2 | 40,029 | Shawn Estes | Mark Brownson | Curt Leskanic | John Johnstone | Dave Veres | 337 | 321 | 16 |
| 1999-06-15 | @ COL | 65 | L 6-15 | 37-28 | 1 | 40,037 | Chris Brock | Brian Bohanon | Brian Bohanon | Chris Brock | | 343 | 336 | 7 |
| 1999-06-16 | @ COL | 66 | W 15-2 | 37-29 | 2 | 41,307 | Mark Gardner | Darryl Kile | Mark Gardner | Darryl Kile | | 358 | 338 | 20 |
| 1999-06-17 | vs CHN | 67 | W 3-2 | 38-29 | 1 | 18,886 | Kirk Rueter | Terry Mulholland | Robb Nen | Dan Serafini | | 361 | 340 | 21 |
| 1999-06-18 | vs CHN | 68 | W 8-5 | 39-29 | 1 | 22,357 | Russ Ortiz | Kevin Tapani | Russ Ortiz | Kevin Tapani | Robb Nen | 369 | 345 | 24 |
| 1999-06-19 | vs CHN | 69 | W 11-5 | 39-30 | 1 | 36,550 | Shawn Estes | Kyle Farnsworth | Shawn Estes | Kyle Farnsworth | | 380 | 350 | 30 |
| 1999-06-20 | vs CHN | 70 | W 7-6 | 40-30 | 1 | 53,245 | Chris Brock | Jon Lieber | Alan Embree | Rick Aguilera | | 387 | 356 | 31 |
| 1999-06-21 | vs MIL | 71 | L 1-8 | 40-31 | 2 | 11,667 | Mark Gardner | Hideo Nomo | Hideo Nomo | Mark Gardner | | 388 | 364 | 24 |
| 1999-06-22 | vs MIL | 72 | L 1-5 | 40-32 | 2 | 10,662 | Kirk Rueter | Scott Karl | Scott Karl | Kirk Rueter | | 389 | 369 | 20 |
| 1999-06-23 | vs MIL | 73 | L 6-9 | 40-33 | 2 | 14,478 | Russ Ortiz | Steve Woodard | Steve Woodard | Russ Ortiz | Bob Wickman | 395 | 378 | 17 |
| 1999-06-25 | vs LAN | 74 | L 2-4 | 40-34 | 2 | 36,849 | Shawn Estes | Kevin Brown | Kevin Brown | Shawn Estes | Jeff Shaw | 397 | 382 | 15 |
| 1999-06-26 | vs LAN | 75 | L 6-7 | 40-35 | 2 | 44,766 | Chris Brock | Carlos Perez | Alan Mills | Robb Nen | Jeff Shaw | 403 | 389 | 14 |
| 1999-06-27 | vs LAN | 76 | W 8-7 | 41-35 | 2 | 42,530 | Mark Gardner | Chan Ho Park | Mark Gardner | Chan Ho Park | Robb Nen | 411 | 396 | 15 |
| 1999-06-29 | vs COL | 77 | W 10-1 | 42-35 | 1 | 11,490 | Kirk Rueter | Bobby Jones | Kirk Rueter | Bobby Jones | | 421 | 397 | 24 |
| 1999-06-30 | vs COL | 78 | W 4-1 | 43-35 | 1 | 24,825 | Russ Ortiz | Brian Bohanon | Russ Ortiz | Brian Bohanon | Robb Nen | 425 | 398 | 27 |
| 1999-07-01 | vs COL | 79 | W 7-1 | 44-35 | 1 | 23,172 | Shawn Estes | Darryl Kile | Shawn Estes | Darryl Kile | | 432 | 399 | 33 |
| 1999-07-02 | @ LAN | 80 | W 6-3 | 45-35 | 1 | 53,869 | Chris Brock | Carlos Perez | Chris Brock | Carlos Perez | Robb Nen | 438 | 402 | 36 |
| 1999-07-03 | @ LAN | 81 | W 9-1 | 46-35 | 1 | 41,770 | Mark Gardner | Chan Ho Park | Mark Gardner | Chan Ho Park | | 447 | 403 | 44 |
| 1999-07-04 | @ LAN | 82 | L 1-7 | 46-36 | 1 | 54,731 | Kirk Rueter | Ismael Valdez | Ismael Valdez | Kirk Rueter | | 448 | 410 | 38 |
| 1999-07-05 | @ SDN | 83 | W 4-1 | 47-36 | 1 | 58,333 | Russ Ortiz | Brian Boehringer | Russ Ortiz | Brian Boehringer | | 452 | 411 | 41 |
| 1999-07-06 | @ SDN | 84 | W 10-9 | 47-37 | 1 | 25,435 | Shawn Estes | Matt Clement | Shawn Estes | Matt Clement | John Johnstone | 462 | 420 | 42 |
| 1999-07-07 | @ SDN | 85 | L 2-5 | 47-38 | 1 | 22,403 | Chris Brock | Sterling Hitchcock | Sterling Hitchcock | Chris Brock | Trevor Hoffman | 464 | 425 | 39 |
| 1999-07-09 | vs SLN | 86 | W 5-4 | 48-38 | 1 | 30,802 | Kirk Rueter | Juan Acevedo | Felix Rodriguez | Manny Aybar | | 469 | 429 | 40 |
| 1999-07-10 | vs SLN | 87 | W 4-2 | 49-38 | 1 | 46,043 | Russ Ortiz | Jose Jimenez | Russ Ortiz | Jose Jimenez | John Johnstone | 473 | 431 | 42 |
| 1999-07-11 | vs SLN | 88 | L 4-5 | 49-39 | 1 | 50,435 | Mark Gardner | Kent Bottenfield | Kent Bottenfield | Mark Gardner | Ricky Bottalico | 477 | 436 | 41 |
| 1999-07-15 | @ OAK | 89 | L 9-11 | 50-39 | 1 | 29,428 | Shawn Estes | Kenny Rogers | Doug Jones | Robb Nen | | 486 | 447 | 39 |
| 1999-07-16 | @ OAK | 90 | L 2-4 | 50-40 | 1 | 44,671 | Russ Ortiz | Gil Heredia | Gil Heredia | Russ Ortiz | Billy Taylor | 488 | 451 | 37 |
| 1999-07-17 | @ OAK | 91 | W 7-2 | 51-40 | 1 | 51,263 | Kirk Rueter | Tim Hudson | Kirk Rueter | Buddy Groom | | 495 | 453 | 42 |
| 1999-07-18 | @ TEX | 92 | L 4-5 | 51-41 | 1 | 41,746 | Mark Gardner | Mike Morgan | Mike Morgan | Mark Gardner | John Wetteland | 499 | 458 | 41 |
| 1999-07-19 | @ TEX | 93 | L 7-14 | 52-41 | 1 | 40,976 | Chris Brock | Ryan Glynn | Esteban Loaiza | Chris Brock | | 506 | 472 | 34 |
| 1999-07-20 | @ TEX | 94 | L 3-6 | 52-42 | 1 | 33,922 | Shawn Estes | Rick Helling | Rick Helling | Shawn Estes | | 509 | 478 | 31 |
| 1999-07-21 | vs SDN | 95 | W 10-2 | 52-43 | 1 | 19,616 | Russ Ortiz | Sterling Hitchcock | Russ Ortiz | Sterling Hitchcock | | 519 | 480 | 39 |
| 1999-07-22 | vs SDN | 96 | L 7-8 | 52-44 | 1 | 22,455 | Kirk Rueter | Woody Williams | Woody Williams | Kirk Rueter | Trevor Hoffman | 526 | 488 | 38 |
| 1999-07-23 | vs CIN | 97 | W 6-5 | 53-44 | 1 | 23,100 | Chris Brock | Steve Avery | Jerry Spradlin | Scott Sullivan | Robb Nen | 532 | 493 | 39 |
| 1999-07-24 | vs CIN | 98 | L 6-7 | 53-45 | 1 | 32,118 | Mark Gardner | Pete Harnisch | Scott Williamson | Robb Nen | Danny Graves | 538 | 500 | 38 |
| 1999-07-25 | vs CIN | 99 | L 1-2 | 53-46 | 1 | 34,452 | Shawn Estes | Steve Parris | Stan Belinda | Robb Nen | | 539 | 502 | 37 |
| 1999-07-26 | vs SLN | 100 | W 10-8 | 53-47 | 1 | 35,936 | Russ Ortiz | Jose Jimenez | Felix Rodriguez | Heathcliff Slocumb | Robb Nen | 549 | 510 | 39 |
| 1999-07-27 | vs SLN | 101 | W 2-1 | 54-47 | 1 | 26,338 | Kirk Rueter | Kent Bottenfield | Kirk Rueter | Kent Bottenfield | John Johnstone | 551 | 511 | 40 |
| 1999-07-28 | vs SLN | 102 | L 3-6 | 54-48 | 1 | 38,740 | Livan Hernandez | Darren Oliver | Darren Oliver | Livan Hernandez | Ricky Bottalico | 554 | 517 | 37 |
| 1999-07-30 | @ CIN | 103 | L 4-7 | 54-49 | 1 | 31,946 | Mark Gardner | Denny Neagle | Denny Neagle | Mark Gardner | Scott Williamson | 558 | 524 | 34 |
| 1999-07-31 | @ CIN | 104 | W 11-1 | 55-49 | 1 | 31,771 | Shawn Estes | Ron Villone | Shawn Estes | Ron Villone | | 569 | 525 | 44 |
| 1999-08-01 | @ CIN | 105 | L 1-9 | 55-50 | 1 | 25,426 | Russ Ortiz | Brett Tomko | Brett Tomko | Russ Ortiz | | 570 | 534 | 36 |
| 1999-08-02 | @ ARI | 106 | L 6-16 | 56-50 | 1 | 40,470 | Kirk Rueter | Armando Reynoso | Armando Reynoso | Kirk Rueter | | 576 | 550 | 26 |
| 1999-08-03 | @ ARI | 107 | W 3-1 | 57-50 | 1 | 38,794 | Livan Hernandez | Omar Daal | Livan Hernandez | Omar Daal | Robb Nen | 579 | 551 | 28 |
| 1999-08-04 | @ ARI | 108 | L 4-8 | 57-51 | 1 | 41,503 | Joe Nathan | Brian Anderson | Brian Anderson | Joe Nathan | | 583 | 559 | 24 |
| 1999-08-06 | @ ATL | 109 | L 3-7 | 57-52 | 1 | 49,321 | Shawn Estes | Greg Maddux | Greg Maddux | Shawn Estes | | 586 | 566 | 20 |
| 1999-08-07 | @ ATL | 110 | L 4-15 | 58-52 | 1 | 47,798 | Russ Ortiz | Terry Mulholland | Terry Mulholland | Russ Ortiz | | 590 | 581 | 9 |
| 1999-08-08 | @ ATL | 111 | W 5-2 | 59-52 | 1 | 38,026 | Kirk Rueter | Kevin Millwood | Kirk Rueter | Kevin Millwood | Robb Nen | 595 | 583 | 12 |
| 1999-08-09 | @ FLO | 112 | L 4-5 | 59-53 | 1 | 10,768 | Livan Hernandez | Dennis Springer | Jesus Sanchez | John Johnstone | | 599 | 588 | 11 |
| 1999-08-10 | @ FLO | 113 | L 7-8 | 59-54 | 1 | 13,553 | Mark Gardner | Vladimir Nunez | Brian Edmondson | Felix Rodriguez | | 606 | 596 | 10 |
| 1999-08-11 | @ FLO | 114 | L 5-6 | 59-55 | 1 | 16,709 | Shawn Estes | Alex Fernandez | Jesus Sanchez | Robb Nen | | 611 | 602 | 9 |
| 1999-08-13 | vs NYN | 115 | W 3-2 | 60-55 | 1 | 25,533 | Russ Ortiz | Masato Yoshii | Russ Ortiz | Masato Yoshii | Robb Nen | 614 | 604 | 10 |
| 1999-08-14 | vs NYN | 116 | L 1-6 | 60-56 | 1 | 57,853 | Kirk Rueter | Orel Hershiser | Orel Hershiser | Kirk Rueter | | 615 | 610 | 5 |
| 1999-08-15 | vs NYN | 117 | L 5-12 | 61-56 | 1 | 41,530 | Livan Hernandez | Kenny Rogers | Kenny Rogers | Livan Hernandez | | 620 | 622 | -2 |
| 1999-08-16 | vs MON | 118 | W 7-4 | 62-56 | 1 | 13,299 | Joe Nathan | Tony Armas | Joe Nathan | Tony Armas | Robb Nen | 627 | 626 | 1 |
| 1999-08-17 | vs MON | 119 | L 1-2 | 62-57 | 1 | 13,865 | Shawn Estes | Dustin Hermanson | Dan Smith | John Johnstone | Ugueth Urbina | 628 | 628 | 0 |
| 1999-08-18 | vs MON | 120 | W 5-4 | 63-57 | 1 | 14,358 | Russ Ortiz | Javier Vazquez | Russ Ortiz | Javier Vazquez | Robb Nen | 633 | 632 | 1 |
| 1999-08-20 | @ MIL | 121 | W 10-3 | 63-58 | 1 | 27,762 | Kirk Rueter | Bill Pulsipher | Kirk Rueter | Bill Pulsipher | | 643 | 635 | 8 |
| 1999-08-21 | @ MIL | 122 | W 5-1 | 64-58 | 1 | 25,646 | Livan Hernandez | Kyle Peterson | Livan Hernandez | Kyle Peterson | | 648 | 636 | 12 |
| 1999-08-22 | @ MIL | 123 | W 7-3 | 65-58 | 1 | 22,193 | Joe Nathan | Cal Eldred | Joe Nathan | Cal Eldred | | 655 | 639 | 16 |
| 1999-08-24 | @ CHN | 124 | W 12-4 | 65-59 | 1 | 25,501 | Shawn Estes | Andrew Lorraine | Shawn Estes | Andrew Lorraine | | 667 | 643 | 24 |
| 1999-08-25 | @ CHN | 125 | W 11-5 | 65-60 | 2 | 0 | Russ Ortiz | Kevin Tapani | Russ Ortiz | Kevin Tapani | | 678 | 648 | 30 |
| 1999-08-25 | @ CHN | 126 | W 6-5 | 65-60 | 2 | 26,584 | Kirk Rueter | Jon Lieber | Kirk Rueter | Jon Lieber | Robb Nen | 684 | 653 | 31 |
| 1999-08-26 | @ CHN | 127 | L 10-11 | 66-61 | 1 | 28,351 | Livan Hernandez | Micah Bowie | Terry Adams | Robb Nen | | 694 | 664 | 30 |
| 1999-08-27 | vs PIT | 128 | L 1-4 | 66-62 | 1 | 16,390 | Joe Nathan | Jason Schmidt | Jason Schmidt | Joe Nathan | Mike Williams | 695 | 668 | 27 |
| 1999-08-28 | vs PIT | 129 | W 6-2 | 67-62 | 1 | 32,783 | Mark Gardner | Francisco Cordova | Mark Gardner | Francisco Cordova | | 701 | 670 | 31 |
| 1999-08-29 | vs PIT | 130 | W 5-3 | 68-62 | 1 | 34,020 | Shawn Estes | Kris Benson | Shawn Estes | Kris Benson | Robb Nen | 706 | 673 | 33 |
| 1999-08-30 | vs PHI | 131 | W 6-4 | 69-62 | 1 | 13,193 | Russ Ortiz | Robert Person | Rich Rodriguez | Billy Brewer | | 712 | 677 | 35 |
| 1999-08-31 | vs PHI | 132 | W 8-1 | 70-62 | 1 | 13,106 | Kirk Rueter | Randy Wolf | Kirk Rueter | Randy Wolf | | 720 | 678 | 42 |
| 1999-09-01 | vs PHI | 133 | W 5-3 | 71-62 | 1 | 11,156 | Livan Hernandez | Mike Grace | Rich Rodriguez | Wayne Gomes | | 725 | 681 | 44 |
| 1999-09-02 | vs PHI | 134 | W 3-2 | 72-62 | 1 | 12,299 | Joe Nathan | Joe Grahe | Joe Nathan | Joe Grahe | Robb Nen | 728 | 683 | 45 |
| 1999-09-03 | @ PIT | 135 | W 12-2 | 72-63 | 1 | 16,478 | Shawn Estes | Francisco Cordova | Shawn Estes | Francisco Cordova | | 740 | 685 | 55 |
| 1999-09-04 | @ PIT | 136 | W 9-2 | 73-63 | 1 | 19,949 | Russ Ortiz | Kris Benson | Russ Ortiz | Kris Benson | | 749 | 687 | 62 |
| 1999-09-05 | @ PIT | 137 | L 4-8 | 73-64 | 1 | 17,901 | Kirk Rueter | Chris Peters | Chris Peters | Kirk Rueter | | 753 | 695 | 58 |
| 1999-09-06 | @ NYN | 138 | L 0-3 | 73-65 | 1 | 35,727 | Livan Hernandez | Kenny Rogers | Kenny Rogers | Mark Gardner | | 753 | 698 | 55 |
| 1999-09-07 | @ NYN | 139 | W 7-4 | 74-65 | 1 | 24,002 | Joe Nathan | Rick Reed | Rich Rodriguez | Turk Wendell | Robb Nen | 760 | 702 | 58 |
| 1999-09-08 | @ NYN | 140 | L 5-7 | 74-66 | 1 | 26,499 | Shawn Estes | Octavio Dotel | Octavio Dotel | Shawn Estes | Armando Benitez | 765 | 709 | 56 |
| 1999-09-10 | vs ATL | 141 | L 2-4 | 74-67 | 1 | 23,150 | Russ Ortiz | John Smoltz | Mike Remlinger | Russ Ortiz | John Rocker | 767 | 713 | 54 |
| 1999-09-11 | vs ATL | 142 | W 3-2 | 75-67 | 1 | 35,981 | Kirk Rueter | Tom Glavine | Kirk Rueter | Tom Glavine | Robb Nen | 770 | 715 | 55 |
| 1999-09-12 | vs ATL | 143 | W 8-4 | 76-67 | 1 | 44,402 | Joe Nathan | Greg Maddux | Joe Nathan | Greg Maddux | | 778 | 719 | 59 |
| 1999-09-14 | vs FLO | 144 | W 3-0 | 77-67 | 1 | 16,335 | Shawn Estes | Ryan Dempster | Shawn Estes | Ryan Dempster | | 781 | 719 | 62 |
| 1999-09-15 | vs FLO | 145 | W 4-3 | 78-67 | 1 | 11,996 | Russ Ortiz | Dennis Springer | Russ Ortiz | Dennis Springer | Robb Nen | 785 | 722 | 63 |
| 1999-09-16 | vs FLO | 146 | W 6-5 | 79-67 | 1 | 14,095 | Kirk Rueter | Vladimir Nunez | Bronswell Patrick | Vladimir Nunez | Robb Nen | 791 | 727 | 64 |
| 1999-09-17 | @ SDN | 147 | W 4-2 | 80-67 | 1 | 29,028 | Joe Nathan | Andy Ashby | Joe Nathan | Andy Ashby | Robb Nen | 795 | 729 | 66 |
| 1999-09-18 | @ SDN | 148 | L 5-11 | 81-67 | 1 | 42,265 | Mark Gardner | Sterling Hitchcock | Sterling Hitchcock | Mark Gardner | | 800 | 740 | 60 |
| 1999-09-19 | @ SDN | 149 | L 3-6 | 81-68 | 1 | 32,443 | Shawn Estes | Woody Williams | Woody Williams | Shawn Estes | Trevor Hoffman | 803 | 746 | 57 |
| 1999-09-20 | @ LAN | 150 | L 5-6 | 81-69 | 1 | 33,280 | Russ Ortiz | Eric Gagne | Pedro Borbon | Alan Embree | | 808 | 752 | 56 |
| 1999-09-21 | @ LAN | 151 | L 4-9 | 81-70 | 1 | 31,881 | Kirk Rueter | Jeff Williams | Jeff Williams | Kirk Rueter | | 812 | 761 | 51 |
| 1999-09-22 | @ LAN | 152 | W 5-4 | 82-70 | 1 | 32,624 | Joe Nathan | Ismael Valdez | Mark Gardner | Pedro Borbon | Robb Nen | 817 | 765 | 52 |
| 1999-09-23 | @ LAN | 153 | L 3-5 | 82-71 | 1 | 34,589 | Livan Hernandez | Chan Ho Park | Chan Ho Park | Livan Hernandez | Jeff Shaw | 820 | 770 | 50 |
| 1999-09-24 | vs ARI | 154 | L 3-11 | 83-71 | 1 | 48,149 | Shawn Estes | Randy Johnson | Randy Johnson | Shawn Estes | | 823 | 781 | 42 |
| 1999-09-25 | vs ARI | 155 | L 3-7 | 83-72 | 1 | 40,096 | Russ Ortiz | Todd Stottlemyre | Gregg Olson | Robb Nen | | 826 | 788 | 38 |
| 1999-09-26 | vs ARI | 156 | L 1-7 | 83-73 | 1 | 40,567 | Kirk Rueter | Omar Daal | Omar Daal | Kirk Rueter | | 827 | 795 | 32 |
| 1999-09-28 | vs LAN | 157 | L 3-6 | 83-74 | 1 | 34,786 | Joe Nathan | Chan Ho Park | Chan Ho Park | Joe Nathan | | 830 | 801 | 29 |
| 1999-09-29 | vs LAN | 158 | W 5-1 | 84-74 | 1 | 47,343 | Livan Hernandez | Kevin Brown | Livan Hernandez | Kevin Brown | Bronswell Patrick | 835 | 802 | 33 |
| 1999-09-30 | vs LAN | 159 | L 4-9 | 84-75 | 1 | 61,389 | Shawn Estes | Jeff Williams | Jeff Williams | Shawn Estes | | 839 | 811 | 28 |
| 1999-10-01 | @ COL | 160 | W 9-4 | 85-75 | 1 | 41,302 | Russ Ortiz | John Thomson | Russ Ortiz | John Thomson | | 848 | 815 | 33 |
| 1999-10-02 | @ COL | 161 | W 16-7 | 85-76 | 1 | 38,393 | Kirk Rueter | Jamey Wright | Kirk Rueter | Jamey Wright | | 864 | 822 | 42 |
| 1999-10-03 | @ COL | 162 | L 8-9 | 85-77 | 1 | 40,117 | Joe Nathan | Brian Bohanon | Dave Veres | Alan Embree | | 872 | 831 | 41 |