| 1999-04-05 | @ ATL | 1 | W 7-4 | 1-0 | 3 | 47,522 | Curt Schilling | Tom Glavine | Curt Schilling | Tom Glavine | Jeff Brantley | 7 | 4 | 3 |
| 1999-04-06 | @ ATL | 2 | L 3-11 | 2-0 | 2 | 29,183 | Chad Ogea | Greg Maddux | Greg Maddux | Chad Ogea | Derrin Ebert | 10 | 15 | -5 |
| 1999-04-07 | @ ATL | 3 | L 0-4 | 2-1 | 3 | 32,164 | Carlton Loewer | John Smoltz | John Smoltz | Carlton Loewer | | 10 | 19 | -9 |
| 1999-04-08 | @ ATL | 4 | W 6-3 | 3-1 | 2 | 47,225 | Paul Byrd | Kevin Millwood | Paul Byrd | Kevin Millwood | Jeff Brantley | 16 | 22 | -6 |
| 1999-04-09 | @ FLO | 5 | L 4-7 | 3-2 | 3 | 13,229 | Paul Spoljaric | Brian Meadows | Brian Meadows | Paul Spoljaric | | 20 | 29 | -9 |
| 1999-04-10 | @ FLO | 6 | W 5-2 | 4-2 | 2 | 22,776 | Curt Schilling | Dennis Springer | Curt Schilling | Dennis Springer | Jeff Brantley | 25 | 31 | -6 |
| 1999-04-11 | @ FLO | 7 | W 2-1 | 5-2 | 1 | 14,954 | Chad Ogea | Alex Fernandez | Chad Ogea | Alex Fernandez | Jeff Brantley | 27 | 32 | -5 |
| 1999-04-12 | vs ATL | 8 | L 6-8 | 5-3 | 1 | 37,582 | Carlton Loewer | John Smoltz | Mike Cather | Ken Ryan | Rudy Seanez | 33 | 40 | -7 |
| 1999-04-14 | vs ATL | 9 | L 4-10 | 6-3 | 1 | 16,287 | Paul Byrd | Kevin Millwood | Kevin Millwood | Paul Byrd | | 37 | 50 | -13 |
| 1999-04-16 | vs FLO | 10 | W 17-3 | 6-4 | 1 | 12,079 | Curt Schilling | Dennis Springer | Curt Schilling | Dennis Springer | | 54 | 53 | 1 |
| 1999-04-17 | vs FLO | 11 | W 2-1 | 7-4 | 1 | 14,817 | Chad Ogea | Livan Hernandez | Wayne Gomes | Antonio Alfonseca | | 56 | 54 | 2 |
| 1999-04-18 | vs FLO | 12 | W 7-2 | 8-4 | 1 | 17,176 | Carlton Loewer | Kirt Ojala | Carlton Loewer | Kirt Ojala | | 63 | 56 | 7 |
| 1999-04-19 | @ ARI | 13 | L 2-3 | 8-5 | 1 | 29,704 | Paul Byrd | Omar Daal | Omar Daal | Yorkis Perez | Greg Swindell | 65 | 59 | 6 |
| 1999-04-20 | @ ARI | 14 | L 1-8 | 8-6 | 2 | 30,546 | Paul Spoljaric | Randy Johnson | Randy Johnson | Paul Spoljaric | | 66 | 67 | -1 |
| 1999-04-21 | @ ARI | 15 | L 2-4 | 8-7 | 2 | 31,421 | Curt Schilling | Todd Stottlemyre | Todd Stottlemyre | Curt Schilling | Gregg Olson | 68 | 71 | -3 |
| 1999-04-23 | @ MON | 16 | W 6-2 | 9-7 | 2 | 8,818 | Chad Ogea | Dustin Hermanson | Chad Ogea | Dustin Hermanson | | 74 | 73 | 1 |
| 1999-04-24 | @ MON | 17 | W 6-5 | 10-7 | 1 | 8,212 | Carlton Loewer | Carl Pavano | Mike Grace | Bobby Ayala | Wayne Gomes | 80 | 78 | 2 |
| 1999-04-25 | @ MON | 18 | W 8-6 | 11-7 | 1 | 9,280 | Paul Byrd | Javier Vazquez | Paul Byrd | Ugueth Urbina | | 88 | 84 | 4 |
| 1999-04-27 | vs CIN | 19 | W 1-0 | 12-7 | 1 | 14,114 | Curt Schilling | Denny Neagle | Jeff Brantley | Gabe White | | 89 | 84 | 5 |
| 1999-04-28 | vs CIN | 20 | L 8-12 | 13-7 | 1 | 12,354 | Chad Ogea | Brett Tomko | Scott Williamson | Jeff Brantley | | 97 | 96 | 1 |
| 1999-04-29 | vs CIN | 21 | L 3-7 | 13-8 | 1 | 12,248 | Carlton Loewer | Jason Bere | Jason Bere | Carlton Loewer | | 100 | 103 | -3 |
| 1999-04-30 | vs LAN | 22 | L 3-4 | 13-9 | 1 | 20,024 | Paul Byrd | Carlos Perez | Carlos Perez | Paul Byrd | Jeff Shaw | 103 | 107 | -4 |
| 1999-05-01 | vs LAN | 23 | L 6-12 | 14-9 | 1 | 22,053 | Paul Spoljaric | Darren Dreifort | Darren Dreifort | Paul Spoljaric | | 109 | 119 | -10 |
| 1999-05-02 | vs LAN | 24 | W 12-3 | 14-10 | 2 | 34,608 | Curt Schilling | Kevin Brown | Curt Schilling | Kevin Brown | | 121 | 122 | -1 |
| 1999-05-03 | vs SDN | 25 | L 3-9 | 14-11 | 2 | 11,032 | Chad Ogea | Sterling Hitchcock | Sterling Hitchcock | Chad Ogea | | 124 | 131 | -7 |
| 1999-05-04 | vs SDN | 26 | W 3-0 | 15-11 | 2 | 15,183 | Carlton Loewer | Woody Williams | Carlton Loewer | Woody Williams | | 127 | 131 | -4 |
| 1999-05-05 | vs SDN | 27 | W 11-1 | 16-11 | 1 | 18,229 | Paul Byrd | Stan Spencer | Paul Byrd | Stan Spencer | | 138 | 132 | 6 |
| 1999-05-07 | @ COL | 28 | W 8-1 | 17-11 | 1 | 41,465 | Curt Schilling | John Thomson | Curt Schilling | John Thomson | | 146 | 133 | 13 |
| 1999-05-08 | @ COL | 29 | W 7-2 | 18-11 | 1 | 43,340 | Joel Bennett | Brian Bohanon | Joel Bennett | Brian Bohanon | | 153 | 135 | 18 |
| 1999-05-09 | @ COL | 30 | W 10-8 | 18-12 | 2 | 40,251 | Chad Ogea | Darryl Kile | Ken Ryan | Dave Veres | Wayne Gomes | 163 | 143 | 20 |
| 1999-05-10 | @ SLN | 31 | L 2-5 | 18-13 | 2 | 34,789 | Carlton Loewer | Kent Bottenfield | Kent Bottenfield | Carlton Loewer | Scott Radinsky | 165 | 148 | 17 |
| 1999-05-11 | @ SLN | 32 | W 9-4 | 19-13 | 2 | 32,307 | Paul Byrd | Kent Mercker | Paul Byrd | Kent Mercker | | 174 | 152 | 22 |
| 1999-05-12 | @ SLN | 33 | W 8-4 | 20-13 | 1 | 45,540 | Curt Schilling | Darren Oliver | Curt Schilling | Darren Oliver | | 182 | 156 | 26 |
| 1999-05-14 | vs NYN | 34 | L 3-7 | 20-14 | 2 | 21,074 | Chad Ogea | Masato Yoshii | Masato Yoshii | Chad Ogea | | 185 | 163 | 22 |
| 1999-05-15 | vs NYN | 35 | L 7-9 | 20-15 | 2 | 27,039 | Carlton Loewer | Al Leiter | Pat Mahomes | Ken Ryan | John Franco | 192 | 172 | 20 |
| 1999-05-16 | vs NYN | 36 | W 5-2 | 21-15 | 2 | 28,422 | Paul Byrd | Orel Hershiser | Paul Byrd | Orel Hershiser | Jeff Brantley | 197 | 174 | 23 |
| 1999-05-17 | @ MON | 37 | W 4-3 | 22-15 | 1 | 5,104 | Curt Schilling | Mike Thurman | Curt Schilling | Mike Thurman | | 201 | 177 | 24 |
| 1999-05-18 | @ MON | 38 | L 4-7 | 22-16 | 1 | 4,660 | Joel Bennett | Miguel Batista | Miguel Batista | Joel Bennett | Ugueth Urbina | 205 | 184 | 21 |
| 1999-05-19 | @ MON | 39 | L 9-10 | 23-16 | 1 | 5,182 | Chad Ogea | Dustin Hermanson | Steve Kline | Jeff Brantley | | 214 | 194 | 20 |
| 1999-05-21 | @ NYN | 40 | L 5-7 | 23-17 | 2 | 24,554 | Carlton Loewer | Orel Hershiser | Orel Hershiser | Carlton Loewer | John Franco | 219 | 201 | 18 |
| 1999-05-22 | @ NYN | 41 | W 9-3 | 24-17 | 1 | 34,575 | Paul Byrd | Bobby Jones | Paul Byrd | Bobby Jones | | 228 | 204 | 24 |
| 1999-05-23 | @ NYN | 42 | L 4-5 | 24-18 | 2 | 34,950 | Curt Schilling | Rick Reed | Rigo Beltran | Curt Schilling | | 232 | 209 | 23 |
| 1999-05-24 | vs MON | 43 | W 5-4 | 25-18 | 1 | 13,953 | Joel Bennett | Miguel Batista | Yorkis Perez | Miguel Batista | Wayne Gomes | 237 | 213 | 24 |
| 1999-05-25 | vs MON | 44 | L 2-4 | 25-19 | 2 | 15,876 | Chad Ogea | Dustin Hermanson | Ugueth Urbina | Steve Montgomery | | 239 | 217 | 22 |
| 1999-05-26 | vs MON | 45 | L 2-5 | 25-20 | 2 | 13,168 | Carlton Loewer | Carl Pavano | Carl Pavano | Carlton Loewer | Ugueth Urbina | 241 | 222 | 19 |
| 1999-05-28 | vs COL | 46 | L 3-5 | 25-21 | 2 | 16,365 | Paul Byrd | Mark Brownson | Curt Leskanic | Paul Byrd | Dave Veres | 244 | 227 | 17 |
| 1999-05-29 | vs COL | 47 | W 2-0 | 26-21 | 2 | 22,204 | Curt Schilling | Brian Bohanon | Curt Schilling | Brian Bohanon | | 246 | 227 | 19 |
| 1999-05-30 | vs COL | 48 | L 0-1 | 26-22 | 2 | 30,358 | Chad Ogea | Darryl Kile | Darryl Kile | Jim Poole | Dave Veres | 246 | 228 | 18 |
| 1999-05-31 | vs SFN | 49 | W 4-3 | 27-22 | 1 | 16,323 | Carlton Loewer | Kirk Rueter | Yorkis Perez | John Johnstone | Wayne Gomes | 250 | 231 | 19 |
| 1999-06-01 | vs SFN | 50 | L 5-6 | 27-23 | 1 | 13,050 | Robert Person | Mark Gardner | Robb Nen | Wayne Gomes | | 255 | 237 | 18 |
| 1999-06-02 | vs SFN | 51 | W 7-6 | 28-23 | 1 | 13,616 | Paul Byrd | Russ Ortiz | Paul Byrd | Russ Ortiz | Wayne Gomes | 262 | 243 | 19 |
| 1999-06-03 | vs SFN | 52 | L 4-7 | 28-24 | 1 | 20,560 | Curt Schilling | Shawn Estes | Jerry Spradlin | Curt Schilling | Robb Nen | 266 | 250 | 16 |
| 1999-06-04 | @ BAL | 53 | W 9-5 | 29-24 | 1 | 47,542 | Chad Ogea | Scott Erickson | Chad Ogea | Scott Erickson | | 275 | 255 | 20 |
| 1999-06-05 | @ BAL | 54 | L 6-7 | 29-25 | 1 | 48,531 | Carlton Loewer | Sidney Ponson | Mike Timlin | Steve Montgomery | | 281 | 262 | 19 |
| 1999-06-06 | @ BAL | 55 | W 11-7 | 29-26 | 1 | 47,833 | Robert Person | Juan Guzman | Joel Bennett | Ricky Bones | | 292 | 269 | 23 |
| 1999-06-07 | vs NYA | 56 | W 6-5 | 30-26 | 1 | 37,180 | Paul Byrd | Andy Pettitte | Paul Byrd | Andy Pettitte | | 298 | 274 | 24 |
| 1999-06-08 | vs NYA | 57 | W 11-5 | 30-27 | 1 | 44,444 | Curt Schilling | Hideki Irabu | Yorkis Perez | Jason Grimsley | | 309 | 279 | 30 |
| 1999-06-09 | vs NYA | 58 | L 5-11 | 31-27 | 1 | 42,047 | Chad Ogea | David Cone | David Cone | Chad Ogea | | 314 | 290 | 24 |
| 1999-06-11 | vs TOR | 59 | W 8-4 | 32-27 | 1 | 26,541 | Randy Wolf | Joey Hamilton | Randy Wolf | Joey Hamilton | | 322 | 294 | 28 |
| 1999-06-12 | vs TOR | 60 | W 7-2 | 33-27 | 1 | 20,449 | Paul Byrd | Kelvim Escobar | Paul Byrd | Kelvim Escobar | | 329 | 296 | 33 |
| 1999-06-13 | vs TOR | 61 | L 2-7 | 33-28 | 1 | 28,459 | Curt Schilling | Pat Hentgen | Pat Hentgen | Curt Schilling | | 331 | 303 | 28 |
| 1999-06-15 | @ SDN | 62 | L 1-6 | 33-29 | 1 | 16,134 | Chad Ogea | Matt Clement | Matt Clement | Chad Ogea | | 332 | 309 | 23 |
| 1999-06-16 | @ SDN | 63 | W 4-2 | 34-29 | 1 | 15,136 | Randy Wolf | Sterling Hitchcock | Randy Wolf | Sterling Hitchcock | Wayne Gomes | 336 | 311 | 25 |
| 1999-06-17 | @ SDN | 64 | W 7-5 | 35-29 | 1 | 16,671 | Paul Byrd | Woody Williams | Paul Byrd | Woody Williams | Wayne Gomes | 343 | 316 | 27 |
| 1999-06-18 | @ LAN | 65 | W 2-1 | 36-29 | 1 | 41,590 | Curt Schilling | Ismael Valdez | Curt Schilling | Ismael Valdez | Wayne Gomes | 345 | 317 | 28 |
| 1999-06-19 | @ LAN | 66 | L 1-8 | 36-30 | 1 | 32,315 | Robert Person | Darren Dreifort | Darren Dreifort | Robert Person | | 346 | 325 | 21 |
| 1999-06-20 | @ LAN | 67 | L 2-3 | 36-31 | 1 | 46,347 | Chad Ogea | Kevin Brown | Kevin Brown | Chad Ogea | Jeff Shaw | 348 | 328 | 20 |
| 1999-06-22 | vs PIT | 68 | W 3-2 | 37-31 | 1 | 18,835 | Randy Wolf | Francisco Cordova | Randy Wolf | Francisco Cordova | Wayne Gomes | 351 | 330 | 21 |
| 1999-06-23 | vs PIT | 69 | L 6-8 | 37-32 | 2 | 20,256 | Paul Byrd | Kris Benson | Kris Benson | Paul Byrd | Mike Williams | 357 | 338 | 19 |
| 1999-06-24 | vs PIT | 70 | W 7-5 | 38-32 | 2 | 25,848 | Curt Schilling | Jose Silva | Curt Schilling | Jose Silva | Wayne Gomes | 364 | 343 | 21 |
| 1999-06-25 | @ CHN | 71 | W 3-2 | 39-32 | 1 | 40,553 | Chad Ogea | Jon Lieber | Chad Ogea | Jon Lieber | Wayne Gomes | 367 | 345 | 22 |
| 1999-06-26 | @ CHN | 72 | W 6-2 | 40-32 | 1 | 40,466 | Robert Person | Steve Trachsel | Robert Person | Steve Trachsel | | 373 | 347 | 26 |
| 1999-06-27 | @ CHN | 73 | L 7-13 | 41-32 | 1 | 38,455 | Randy Wolf | Terry Mulholland | Terry Mulholland | Mike Grace | | 380 | 360 | 20 |
| 1999-06-28 | @ PIT | 74 | L 2-3 | 41-33 | 1 | 14,144 | Paul Byrd | Kris Benson | Greg Hansell | Steve Montgomery | | 382 | 363 | 19 |
| 1999-06-29 | @ PIT | 75 | W 7-4 | 42-33 | 1 | 16,343 | Curt Schilling | Jose Silva | Curt Schilling | Jose Silva | | 389 | 367 | 22 |
| 1999-06-30 | @ PIT | 76 | L 1-9 | 42-34 | 1 | 14,526 | Chad Ogea | Jason Schmidt | Jason Schmidt | Chad Ogea | | 390 | 376 | 14 |
| 1999-07-01 | @ PIT | 77 | L 7-12 | 43-34 | 1 | 11,174 | Robert Person | Todd Ritchie | Todd Ritchie | Robert Person | | 397 | 388 | 9 |
| 1999-07-02 | vs CHN | 78 | W 14-1 | 44-34 | 1 | 50,498 | Randy Wolf | Terry Mulholland | Randy Wolf | Terry Mulholland | | 411 | 389 | 22 |
| 1999-07-03 | vs CHN | 79 | W 21-8 | 44-35 | 1 | 58,086 | Paul Byrd | Kyle Farnsworth | Paul Byrd | Kyle Farnsworth | | 432 | 397 | 35 |
| 1999-07-04 | vs CHN | 80 | W 6-2 | 45-35 | 1 | 20,097 | Curt Schilling | Kevin Tapani | Curt Schilling | Kevin Tapani | | 438 | 399 | 39 |
| 1999-07-05 | vs MIL | 81 | L 0-5 | 45-36 | 1 | 13,248 | Chad Ogea | Jim Abbott | Jim Abbott | Chad Ogea | Rafael Roque | 438 | 404 | 34 |
| 1999-07-06 | vs MIL | 82 | W 1-0 | 46-36 | 1 | 13,006 | Robert Person | Hideo Nomo | Robert Person | Hideo Nomo | Wayne Gomes | 439 | 404 | 35 |
| 1999-07-07 | vs MIL | 83 | W 5-4 | 47-36 | 1 | 16,593 | Randy Wolf | Scott Karl | Wayne Gomes | Bob Wickman | | 444 | 408 | 36 |
| 1999-07-09 | vs BAL | 84 | W 4-2 | 48-36 | 1 | 28,182 | Curt Schilling | Juan Guzman | Curt Schilling | Juan Guzman | | 448 | 410 | 38 |
| 1999-07-10 | vs BAL | 85 | L 4-8 | 48-37 | 1 | 32,300 | Paul Byrd | Mike Mussina | Mike Mussina | Paul Byrd | | 452 | 418 | 34 |
| 1999-07-11 | vs BAL | 86 | L 2-6 | 48-38 | 1 | 33,399 | Chad Ogea | Scott Erickson | Scott Erickson | Chad Ogea | | 454 | 424 | 30 |
| 1999-07-15 | @ BOS | 87 | L 4-6 | 48-39 | 1 | 32,397 | Paul Byrd | Brian Rose | Brian Rose | Paul Byrd | Tim Wakefield | 458 | 430 | 28 |
| 1999-07-16 | @ BOS | 88 | W 5-4 | 49-39 | 1 | 32,899 | Robert Person | Bret Saberhagen | Robert Person | Bret Saberhagen | Wayne Gomes | 463 | 434 | 29 |
| 1999-07-17 | @ BOS | 89 | W 11-3 | 49-40 | 1 | 32,228 | Randy Wolf | Mark Portugal | Randy Wolf | Mark Portugal | | 474 | 437 | 37 |
| 1999-07-18 | @ TBA | 90 | W 3-2 | 50-40 | 1 | 20,075 | Curt Schilling | Ryan Rupe | Curt Schilling | Albie Lopez | | 477 | 439 | 38 |
| 1999-07-19 | @ TBA | 91 | W 16-3 | 50-41 | 1 | 17,600 | Chad Ogea | Bryan Rekar | Chad Ogea | Bryan Rekar | | 493 | 442 | 51 |
| 1999-07-20 | @ TBA | 92 | L 4-5 | 50-42 | 1 | 30,868 | Paul Byrd | Rolando Arrojo | Norm Charlton | Steve Schrenk | | 497 | 447 | 50 |
| 1999-07-21 | @ MIL | 93 | W 7-0 | 51-42 | 1 | 21,933 | Robert Person | Scott Karl | Robert Person | Scott Karl | Jim Poole | 504 | 447 | 57 |
| 1999-07-22 | @ MIL | 94 | L 0-5 | 51-43 | 1 | 29,777 | Randy Wolf | Hideo Nomo | Hideo Nomo | Randy Wolf | | 504 | 452 | 52 |
| 1999-07-23 | vs ATL | 95 | W 6-5 | 52-44 | 2 | 0 | Curt Schilling | Kevin Millwood | Amaury Telemaco | Rudy Seanez | Wayne Gomes | 510 | 457 | 53 |
| 1999-07-23 | vs ATL | 96 | L 1-3 | 52-44 | 2 | 32,673 | Anthony Shumaker | Bruce Chen | Bruce Chen | Anthony Shumaker | John Rocker | 511 | 460 | 51 |
| 1999-07-24 | vs ATL | 97 | W 4-3 | 53-44 | 1 | 30,167 | Chad Ogea | John Smoltz | Steve Montgomery | Micah Bowie | Wayne Gomes | 515 | 463 | 52 |
| 1999-07-25 | vs ATL | 98 | L 4-5 | 53-45 | 2 | 25,659 | Paul Byrd | Tom Glavine | John Rocker | Steve Montgomery | | 519 | 468 | 51 |
| 1999-07-26 | vs FLO | 99 | W 9-1 | 54-45 | 2 | 16,047 | Robert Person | Vladimir Nunez | Robert Person | Vladimir Nunez | | 528 | 469 | 59 |
| 1999-07-27 | vs FLO | 100 | L 2-6 | 54-46 | 2 | 18,282 | Randy Wolf | Alex Fernandez | Alex Fernandez | Randy Wolf | Antonio Alfonseca | 530 | 475 | 55 |
| 1999-07-28 | vs FLO | 101 | W 9-4 | 55-46 | 2 | 17,497 | Steve Schrenk | Ryan Dempster | Steve Schrenk | Ryan Dempster | | 539 | 479 | 60 |
| 1999-07-29 | vs FLO | 102 | W 12-1 | 56-46 | 2 | 26,834 | Chad Ogea | Brian Meadows | Chad Ogea | Brian Meadows | | 551 | 480 | 71 |
| 1999-07-30 | @ ATL | 103 | W 9-2 | 57-46 | 1 | 48,605 | Paul Byrd | John Smoltz | Paul Byrd | John Smoltz | | 560 | 482 | 78 |
| 1999-07-31 | @ ATL | 104 | L 6-8 | 57-47 | 1 | 50,203 | Robert Person | Tom Glavine | Tom Glavine | Robert Person | John Rocker | 566 | 490 | 76 |
| 1999-08-01 | @ ATL | 105 | L 4-12 | 58-47 | 1 | 37,521 | Randy Wolf | Greg Maddux | Greg Maddux | Randy Wolf | | 570 | 502 | 68 |
| 1999-08-03 | @ FLO | 106 | W 6-5 | 59-47 | 1 | 10,223 | Chad Ogea | Ryan Dempster | Amaury Telemaco | Brian Edmondson | Wayne Gomes | 576 | 507 | 69 |
| 1999-08-04 | @ FLO | 107 | W 4-1 | 60-47 | 1 | 10,445 | Paul Byrd | Dennis Springer | Paul Byrd | Dennis Springer | Steve Schrenk | 580 | 508 | 72 |
| 1999-08-05 | @ FLO | 108 | W 9-3 | 61-47 | 1 | 9,610 | Robert Person | Vladimir Nunez | Robert Person | Vladimir Nunez | | 589 | 511 | 78 |
| 1999-08-06 | vs ARI | 109 | W 4-2 | 62-47 | 1 | 27,742 | Randy Wolf | Randy Johnson | Wayne Gomes | Bobby Chouinard | | 593 | 513 | 80 |
| 1999-08-07 | vs ARI | 110 | L 2-8 | 62-48 | 1 | 18,766 | Curt Schilling | Andy Benes | Andy Benes | Curt Schilling | | 595 | 521 | 74 |
| 1999-08-08 | vs ARI | 111 | L 4-7 | 62-49 | 1 | 32,047 | Chad Ogea | Armando Reynoso | Armando Reynoso | Chad Ogea | Matt Mantei | 599 | 528 | 71 |
| 1999-08-09 | vs SLN | 112 | L 6-12 | 63-49 | 1 | 46,102 | Steve Schrenk | Kent Mercker | Kent Mercker | Steve Schrenk | | 605 | 540 | 65 |
| 1999-08-10 | vs SLN | 113 | W 7-5 | 64-49 | 1 | 48,514 | Robert Person | Jose Jimenez | Jim Poole | Ricky Bottalico | Wayne Gomes | 612 | 545 | 67 |
| 1999-08-11 | vs SLN | 114 | L 1-5 | 64-50 | 1 | 45,830 | Randy Wolf | Garrett Stephenson | Garrett Stephenson | Randy Wolf | Heathcliff Slocumb | 613 | 550 | 63 |
| 1999-08-13 | @ CIN | 115 | L 4-5 | 64-51 | 1 | 26,353 | Paul Byrd | Brett Tomko | Scott Williamson | Steve Schrenk | | 617 | 555 | 62 |
| 1999-08-14 | @ CIN | 116 | L 1-4 | 64-52 | 1 | 25,214 | Chad Ogea | Pete Harnisch | Pete Harnisch | Chad Ogea | Danny Graves | 618 | 559 | 59 |
| 1999-08-15 | @ CIN | 117 | W 9-3 | 65-52 | 1 | 27,059 | Robert Person | Denny Neagle | Robert Person | Denny Neagle | | 627 | 562 | 65 |
| 1999-08-16 | @ SLN | 118 | L 3-4 | 65-53 | 1 | 36,741 | Randy Wolf | Kent Mercker | Kent Mercker | Randy Wolf | Ricky Bottalico | 630 | 566 | 64 |
| 1999-08-17 | @ SLN | 119 | L 5-6 | 65-54 | 1 | 38,557 | Anthony Shumaker | Garrett Stephenson | Juan Acevedo | Wayne Gomes | | 635 | 572 | 63 |
| 1999-08-18 | @ SLN | 120 | W 6-5 | 66-54 | 1 | 38,047 | Chad Ogea | Kent Bottenfield | Scott Aldred | Rich Croushore | Wayne Gomes | 641 | 577 | 64 |
| 1999-08-20 | vs LAN | 121 | L 5-8 | 66-55 | 2 | 17,444 | Robert Person | Kevin Brown | Alan Mills | Wayne Gomes | | 646 | 585 | 61 |
| 1999-08-21 | vs LAN | 122 | W 6-5 | 67-55 | 2 | 22,078 | Randy Wolf | Ismael Valdez | Wayne Gomes | Onan Masaoka | | 652 | 590 | 62 |
| 1999-08-22 | vs LAN | 123 | L 7-9 | 67-56 | 3 | 22,510 | Anthony Shumaker | Chan Ho Park | Chan Ho Park | Anthony Shumaker | Jeff Shaw | 659 | 599 | 60 |
| 1999-08-23 | vs SDN | 124 | L 6-7 | 67-57 | 3 | 18,759 | Chad Ogea | Woody Williams | Woody Williams | Chad Ogea | Trevor Hoffman | 665 | 606 | 59 |
| 1999-08-24 | vs SDN | 125 | W 18-2 | 67-58 | 3 | 18,126 | Paul Byrd | Stan Spencer | Paul Byrd | Stan Spencer | | 683 | 608 | 75 |
| 1999-08-25 | vs SDN | 126 | W 15-1 | 68-58 | 3 | 25,539 | Robert Person | Matt Clement | Robert Person | Matt Clement | | 698 | 609 | 89 |
| 1999-08-28 | @ COL | 127 | L 6-11 | 69-59 | 4 | 42,744 | Chad Ogea | Jamey Wright | David Lee | Scott Aldred | | 704 | 620 | 84 |
| 1999-08-28 | @ COL | 128 | L 0-4 | 69-59 | 4 | 47,217 | Joe Grahe | Brian Bohanon | Brian Bohanon | Joe Grahe | | 704 | 624 | 80 |
| 1999-08-29 | @ COL | 129 | L 5-6 | 69-60 | 3 | 43,344 | Paul Byrd | Darryl Kile | Darryl Kile | Paul Byrd | Dave Veres | 709 | 630 | 79 |
| 1999-08-30 | @ SFN | 130 | L 4-6 | 69-61 | 3 | 13,193 | Robert Person | Russ Ortiz | Rich Rodriguez | Billy Brewer | | 713 | 636 | 77 |
| 1999-08-31 | @ SFN | 131 | L 1-8 | 69-62 | 3 | 13,106 | Randy Wolf | Kirk Rueter | Kirk Rueter | Randy Wolf | | 714 | 644 | 70 |
| 1999-09-01 | @ SFN | 132 | L 3-5 | 69-63 | 3 | 11,156 | Mike Grace | Livan Hernandez | Rich Rodriguez | Wayne Gomes | | 717 | 649 | 68 |
| 1999-09-02 | @ SFN | 133 | L 2-3 | 69-64 | 3 | 12,299 | Joe Grahe | Joe Nathan | Joe Nathan | Joe Grahe | Robb Nen | 719 | 652 | 67 |
| 1999-09-03 | vs CIN | 134 | W 10-2 | 69-65 | 3 | 14,447 | Curt Schilling | Steve Parris | Curt Schilling | Steve Parris | | 729 | 654 | 75 |
| 1999-09-04 | vs CIN | 135 | L 3-22 | 70-65 | 3 | 16,357 | Paul Byrd | Pete Harnisch | Pete Harnisch | Paul Byrd | Stan Belinda | 732 | 676 | 56 |
| 1999-09-05 | vs CIN | 136 | L 7-9 | 70-66 | 3 | 18,839 | Robert Person | Denny Neagle | Denny Neagle | Robert Person | Scott Sullivan | 739 | 685 | 54 |
| 1999-09-06 | vs HOU | 137 | L 5-6 | 70-67 | 3 | 12,223 | Randy Wolf | Jose Lima | Jose Lima | Randy Wolf | Billy Wagner | 744 | 691 | 53 |
| 1999-09-07 | vs HOU | 138 | L 6-8 | 70-68 | 3 | 12,934 | Mike Grace | Chris Holt | Jay Powell | Wayne Gomes | Doug Henry | 750 | 699 | 51 |
| 1999-09-08 | vs HOU | 139 | L 2-10 | 71-68 | 3 | 14,050 | Curt Schilling | Mike Hampton | Mike Hampton | Curt Schilling | | 752 | 709 | 43 |
| 1999-09-09 | vs HOU | 140 | L 1-3 | 71-69 | 3 | 11,133 | Paul Byrd | Shane Reynolds | Shane Reynolds | Steve Montgomery | Billy Wagner | 753 | 712 | 41 |
| 1999-09-10 | @ ARI | 141 | L 1-3 | 71-70 | 3 | 34,700 | Robert Person | Randy Johnson | Randy Johnson | Robert Person | | 754 | 715 | 39 |
| 1999-09-11 | @ ARI | 142 | L 0-4 | 71-71 | 3 | 42,442 | Randy Wolf | Andy Benes | Andy Benes | Randy Wolf | | 754 | 719 | 35 |
| 1999-09-12 | @ ARI | 143 | L 0-5 | 71-72 | 3 | 32,468 | Mike Grace | Todd Stottlemyre | Todd Stottlemyre | Mike Grace | | 754 | 724 | 30 |
| 1999-09-13 | @ HOU | 144 | L 2-13 | 72-72 | 3 | 44,399 | Joe Grahe | Mike Hampton | Mike Hampton | Joe Grahe | | 756 | 737 | 19 |
| 1999-09-14 | @ HOU | 145 | L 2-12 | 73-72 | 3 | 25,164 | Paul Byrd | Shane Reynolds | Shane Reynolds | Paul Byrd | | 758 | 749 | 9 |
| 1999-09-15 | @ HOU | 146 | W 8-6 | 74-72 | 3 | 31,186 | Robert Person | Scott Elarton | Wayne Gomes | Doug Henry | Billy Brewer | 766 | 755 | 11 |
| 1999-09-17 | @ NYN | 147 | W 8-5 | 75-72 | 3 | 31,842 | Randy Wolf | Al Leiter | Randy Wolf | Al Leiter | Billy Brewer | 774 | 760 | 14 |
| 1999-09-18 | @ NYN | 148 | L 1-11 | 75-73 | 3 | 37,655 | Mike Grace | Masato Yoshii | Masato Yoshii | Mike Grace | | 775 | 771 | 4 |
| 1999-09-19 | @ NYN | 149 | L 6-8 | 75-74 | 3 | 51,560 | Paul Byrd | Kenny Rogers | Octavio Dotel | Paul Byrd | Armando Benitez | 781 | 779 | 2 |
| 1999-09-20 | @ MIL | 150 | L 4-5 | 75-75 | 3 | 10,981 | Robert Person | Scott Karl | Rocky Coppinger | Carlton Loewer | Bob Wickman | 785 | 784 | 1 |
| 1999-09-21 | @ MIL | 151 | L 6-8 | 75-76 | 3 | 11,371 | Anthony Shumaker | Bill Pulsipher | Bill Pulsipher | Anthony Shumaker | Bob Wickman | 791 | 792 | -1 |
| 1999-09-22 | @ MIL | 152 | W 12-3 | 75-77 | 3 | 13,043 | Randy Wolf | Steve Woodard | Amaury Telemaco | Kyle Peterson | | 803 | 795 | 8 |
| 1999-09-23 | @ MIL | 153 | L 6-11 | 76-77 | 3 | 10,887 | Mike Grace | Jason Bere | Jason Bere | Mike Grace | | 809 | 806 | 3 |
| 1999-09-24 | vs NYN | 154 | W 3-2 | 77-77 | 3 | 21,649 | Joe Grahe | Masato Yoshii | Joe Grahe | Armando Benitez | Scott Aldred | 812 | 808 | 4 |
| 1999-09-25 | vs NYN | 155 | W 4-2 | 78-77 | 3 | 23,319 | Robert Person | Kenny Rogers | Robert Person | Kenny Rogers | Wayne Gomes | 816 | 810 | 6 |
| 1999-09-26 | vs NYN | 156 | W 3-2 | 79-77 | 3 | 26,370 | Paul Byrd | Rick Reed | Paul Byrd | Rick Reed | Steve Montgomery | 819 | 812 | 7 |
| 1999-09-28 | vs CHN | 157 | L 2-8 | 79-78 | 3 | 16,106 | Randy Wolf | Steve Trachsel | Steve Trachsel | Randy Wolf | | 821 | 820 | 1 |
| 1999-09-29 | vs CHN | 158 | W 5-0 | 80-78 | 3 | 21,142 | Carlton Loewer | Micah Bowie | Billy Brewer | Micah Bowie | | 826 | 820 | 6 |
| 1999-09-30 | vs CHN | 159 | W 2-1 | 81-78 | 3 | 17,475 | Robert Person | Brian McNichol | Robert Person | Brian McNichol | Steve Montgomery | 828 | 821 | 7 |
| 1999-10-01 | vs MON | 160 | L 4-7 | 81-79 | 3 | 12,652 | Joe Grahe | Javier Vazquez | Javier Vazquez | Joe Grahe | Ugueth Urbina | 832 | 828 | 4 |
| 1999-10-02 | vs MON | 161 | L 3-13 | 82-79 | 3 | 12,871 | Paul Byrd | Jeremy Powell | Jeremy Powell | Paul Byrd | Miguel Batista | 835 | 841 | -6 |
| 1999-10-03 | vs MON | 162 | W 6-5 | 83-79 | 3 | 23,892 | Randy Wolf | Dustin Hermanson | Cliff Politte | Scott Strickland | Steve Montgomery | 841 | 846 | -5 |