Oldest Player: Charlie O'Brien (38)
Youngest Player: Mike Colangelo (22)
Longest Tenure: Tim Salmon, Mike Holtz, Shigetoshi Hasegawa, Randy Velarde, Jim Edmonds, Todd Greene, Gary DiSarcina, Ken Hill, Garret Anderson, Chuck Finley, Troy Percival, Orlando Palmeiro, Darin Erstad (3)
Top Hitter: Randy Velarde (28)
Top Pitcher: Chuck Finley (13)
Top Draft Pick: John Lackey (#68)
Roster Continuity: 62.47%
Top Prospect: Ramon Ortiz
| 1999-04-06 | vs CLE | 1 | W 6-5 | 1-0 | 1 | 39,936 | Tim Belcher | Jaret Wright | Mike Holtz | Steve Karsay | Troy Percival | 6 | 5 | 1 |
| 1999-04-07 | vs CLE | 2 | L 1-9 | 1-1 | 3 | 21,689 | Ken Hill | Dave Burba | Dave Burba | Ken Hill | | 7 | 14 | -7 |
| 1999-04-08 | vs CLE | 3 | L 1-9 | 1-2 | 3 | 25,084 | Steve Sparks | Bartolo Colon | Bartolo Colon | Steve Sparks | | 8 | 23 | -15 |
| 1999-04-09 | @ TEX | 4 | W 8-4 | 2-2 | 2 | 31,633 | Chuck Finley | John Burkett | Chuck Finley | John Burkett | | 16 | 27 | -11 |
| 1999-04-10 | @ TEX | 5 | W 10-0 | 3-2 | 2 | 37,974 | Omar Olivares | Rick Helling | Omar Olivares | Rick Helling | | 26 | 27 | -1 |
| 1999-04-11 | @ TEX | 6 | L 3-6 | 3-3 | 2 | 23,175 | Tim Belcher | Aaron Sele | Aaron Sele | Tim Belcher | John Wetteland | 29 | 33 | -4 |
| 1999-04-12 | @ TEX | 7 | W 13-5 | 3-4 | 3 | 24,601 | Ken Hill | Mark Clark | Mike Magnante | Mark Clark | | 42 | 38 | 4 |
| 1999-04-13 | @ OAK | 8 | L 2-3 | 3-5 | 3 | 5,377 | Steve Sparks | Mike Oquist | Mike Oquist | Steve Sparks | Billy Taylor | 44 | 41 | 3 |
| 1999-04-14 | @ OAK | 9 | L 5-6 | 3-6 | 4 | 8,377 | Chuck Finley | Kenny Rogers | T.J. Mathews | Chuck Finley | Billy Taylor | 49 | 47 | 2 |
| 1999-04-15 | @ OAK | 10 | W 12-1 | 4-6 | 3 | 7,148 | Omar Olivares | Gil Heredia | Omar Olivares | Gil Heredia | | 61 | 48 | 13 |
| 1999-04-16 | vs SEA | 11 | W 9-5 | 5-6 | 3 | 39,635 | Tim Belcher | Jamie Moyer | Tim Belcher | Jamie Moyer | | 70 | 53 | 17 |
| 1999-04-17 | vs SEA | 12 | L 3-4 | 5-7 | 3 | 43,752 | Ken Hill | Freddy Garcia | Jose Paniagua | Troy Percival | Jose Mesa | 73 | 57 | 16 |
| 1999-04-18 | vs SEA | 13 | L 5-8 | 5-8 | 3 | 37,465 | Steve Sparks | Brett Hinchliffe | Ken Cloude | Steve Sparks | Jose Mesa | 78 | 65 | 13 |
| 1999-04-20 | @ TOR | 14 | L 1-5 | 5-9 | 3 | 23,775 | Chuck Finley | Kelvim Escobar | Kelvim Escobar | Chuck Finley | | 79 | 70 | 9 |
| 1999-04-21 | @ TOR | 15 | L 2-3 | 5-10 | 3 | 23,749 | Omar Olivares | Chris Carpenter | Chris Carpenter | Omar Olivares | Robert Person | 81 | 73 | 8 |
| 1999-04-22 | @ TOR | 16 | L 7-8 | 5-11 | 4 | 28,212 | Tim Belcher | Pat Hentgen | Tom Davey | Mark Petkovsek | Graeme Lloyd | 88 | 81 | 7 |
| 1999-04-23 | @ KCA | 17 | W 4-2 | 6-11 | 3 | 13,209 | Ken Hill | Jose Rosado | Shigetoshi Hasegawa | Jeff Montgomery | Troy Percival | 92 | 83 | 9 |
| 1999-04-24 | @ KCA | 18 | L 3-4 | 6-12 | 4 | 15,664 | Steve Sparks | Jeff Suppan | Jose Santiago | Shigetoshi Hasegawa | | 95 | 87 | 8 |
| 1999-04-26 | vs TOR | 19 | W 4-3 | 7-12 | 4 | 17,324 | Chuck Finley | Chris Carpenter | Troy Percival | Nerio Rodriguez | | 99 | 90 | 9 |
| 1999-04-27 | vs TOR | 20 | L 1-10 | 7-13 | 4 | 17,899 | Omar Olivares | Pat Hentgen | Pat Hentgen | Omar Olivares | | 100 | 100 | 0 |
| 1999-04-28 | vs TOR | 21 | W 12-10 | 8-13 | 3 | 18,304 | Tim Belcher | David Wells | Mark Petkovsek | Graeme Lloyd | Troy Percival | 112 | 110 | 2 |
| 1999-04-29 | vs TOR | 22 | W 17-1 | 9-13 | 3 | 18,346 | Ken Hill | Roy Halladay | Ken Hill | Roy Halladay | | 129 | 111 | 18 |
| 1999-04-30 | vs CHA | 23 | W 3-1 | 10-13 | 3 | 35,053 | Steve Sparks | Jaime Navarro | Mark Petkovsek | Jaime Navarro | Troy Percival | 132 | 112 | 20 |
| 1999-05-01 | vs CHA | 24 | L 5-8 | 10-14 | 3 | 35,296 | Chuck Finley | James Baldwin | David Lundquist | Troy Percival | Bob Howry | 137 | 120 | 17 |
| 1999-05-02 | vs CHA | 25 | W 6-3 | 11-14 | 3 | 34,737 | Omar Olivares | Jim Parque | Omar Olivares | Jim Parque | | 143 | 123 | 20 |
| 1999-05-03 | vs CHA | 26 | L 1-8 | 11-15 | 3 | 31,995 | Tim Belcher | John Snyder | John Snyder | Tim Belcher | | 144 | 131 | 13 |
| 1999-05-04 | @ DET | 27 | L 1-3 | 11-16 | 3 | 13,411 | Ken Hill | Dave Mlicki | Doug Brocail | Mike Holtz | Todd Jones | 145 | 134 | 11 |
| 1999-05-05 | @ DET | 28 | W 4-1 | 12-16 | 3 | 12,676 | Steve Sparks | Jeff Weaver | Steve Sparks | Jeff Weaver | Troy Percival | 149 | 135 | 14 |
| 1999-05-06 | @ DET | 29 | L 2-4 | 12-17 | 3 | 12,510 | Chuck Finley | Bryce Florie | Bryce Florie | Chuck Finley | Todd Jones | 151 | 139 | 12 |
| 1999-05-07 | @ BOS | 30 | L 0-6 | 12-18 | 3 | 32,220 | Omar Olivares | Pedro Martinez | Pedro Martinez | Omar Olivares | | 151 | 145 | 6 |
| 1999-05-08 | @ BOS | 31 | L 1-6 | 12-19 | 3 | 29,385 | Tim Belcher | Juan Pena | Juan Pena | Tim Belcher | Derek Lowe | 152 | 151 | 1 |
| 1999-05-09 | @ BOS | 32 | L 2-4 | 12-20 | 4 | 23,710 | Ken Hill | Mark Portugal | Mark Portugal | Ken Hill | Tim Wakefield | 154 | 155 | -1 |
| 1999-05-11 | @ NYA | 33 | W 9-7 | 13-20 | 4 | 25,313 | Steve Sparks | Andy Pettitte | Mark Petkovsek | Ramiro Mendoza | Troy Percival | 163 | 162 | 1 |
| 1999-05-12 | @ NYA | 34 | W 1-0 | 14-20 | 4 | 23,540 | Chuck Finley | David Cone | Chuck Finley | David Cone | Troy Percival | 164 | 162 | 2 |
| 1999-05-13 | @ NYA | 35 | W 2-0 | 15-20 | 3 | 26,702 | Omar Olivares | Hideki Irabu | Omar Olivares | Hideki Irabu | Troy Percival | 166 | 162 | 4 |
| 1999-05-14 | vs TBA | 36 | W 8-3 | 16-20 | 3 | 35,515 | Tim Belcher | Bobby Witt | Tim Belcher | Bobby Witt | | 174 | 165 | 9 |
| 1999-05-15 | vs TBA | 37 | L 1-3 | 16-21 | 4 | 36,939 | Ken Hill | Tony Saunders | Tony Saunders | Ken Hill | Roberto Hernandez | 175 | 168 | 7 |
| 1999-05-16 | vs TBA | 38 | L 4-7 | 16-22 | 4 | 35,064 | Steve Sparks | Wilson Alvarez | Wilson Alvarez | Steve Sparks | | 179 | 175 | 4 |
| 1999-05-18 | @ BAL | 39 | L 3-5 | 16-23 | 4 | 42,830 | Chuck Finley | Mike Mussina | Mike Mussina | Chuck Finley | Mike Timlin | 182 | 180 | 2 |
| 1999-05-19 | @ BAL | 40 | W 5-4 | 17-23 | 4 | 38,557 | Omar Olivares | Scott Erickson | Al Levine | Mike Timlin | Troy Percival | 187 | 184 | 3 |
| 1999-05-20 | @ BAL | 41 | W 6-4 | 18-23 | 4 | 38,388 | Tim Belcher | Jason Johnson | Tim Belcher | Jason Johnson | Troy Percival | 193 | 188 | 5 |
| 1999-05-21 | @ TBA | 42 | L 9-10 | 19-23 | 4 | 20,687 | Ken Hill | Tony Saunders | Rick White | Mike Magnante | Roberto Hernandez | 202 | 198 | 4 |
| 1999-05-22 | @ TBA | 43 | W 8-6 | 20-23 | 3 | 23,168 | Steve Sparks | Wilson Alvarez | Mark Petkovsek | Alan Newman | Troy Percival | 210 | 204 | 6 |
| 1999-05-23 | @ TBA | 44 | W 4-0 | 21-23 | 3 | 22,522 | Chuck Finley | Ryan Rupe | Chuck Finley | Roberto Hernandez | | 214 | 204 | 10 |
| 1999-05-25 | vs BAL | 45 | W 4-1 | 22-23 | 2 | 20,398 | Omar Olivares | Scott Erickson | Omar Olivares | Scott Erickson | Troy Percival | 218 | 205 | 13 |
| 1999-05-26 | vs BAL | 46 | L 2-3 | 22-24 | 2 | 22,058 | Tim Belcher | Sidney Ponson | Sidney Ponson | Tim Belcher | Arthur Rhodes | 220 | 208 | 12 |
| 1999-05-27 | vs BAL | 47 | L 3-6 | 22-25 | 4 | 24,724 | Ken Hill | Juan Guzman | Juan Guzman | Ken Hill | Mike Timlin | 223 | 214 | 9 |
| 1999-05-28 | vs KCA | 48 | L 4-11 | 23-25 | 4 | 30,946 | Chuck Finley | Kevin Appier | Kevin Appier | Chuck Finley | | 227 | 225 | 2 |
| 1999-05-29 | vs KCA | 49 | W 4-3 | 24-25 | 2 | 29,749 | Steve Sparks | Chris Fussell | Steve Sparks | Chris Fussell | Troy Percival | 231 | 228 | 3 |
| 1999-05-30 | vs KCA | 50 | W 4-3 | 25-25 | 2 | 31,429 | Omar Olivares | Jose Rosado | Omar Olivares | Jose Rosado | Troy Percival | 235 | 231 | 4 |
| 1999-05-31 | vs MIN | 51 | L 2-3 | 25-26 | 2 | 20,466 | Tim Belcher | LaTroy Hawkins | LaTroy Hawkins | Shigetoshi Hasegawa | Mike Trombley | 237 | 234 | 3 |
| 1999-06-01 | vs MIN | 52 | W 5-1 | 26-26 | 2 | 17,003 | Ken Hill | Mike Lincoln | Ken Hill | Mike Lincoln | | 242 | 235 | 7 |
| 1999-06-02 | vs MIN | 53 | W 2-1 | 27-26 | 2 | 17,766 | Chuck Finley | Brad Radke | Chuck Finley | Brad Radke | Troy Percival | 244 | 236 | 8 |
| 1999-06-04 | @ LAN | 54 | L 4-5 | 27-27 | 2 | 49,213 | Omar Olivares | Kevin Brown | Kevin Brown | Omar Olivares | Jeff Shaw | 248 | 241 | 7 |
| 1999-06-05 | @ LAN | 55 | L 4-7 | 27-28 | 2 | 44,779 | Tim Belcher | Chan Ho Park | Onan Masaoka | Tim Belcher | Jeff Shaw | 252 | 248 | 4 |
| 1999-06-06 | @ LAN | 56 | W 7-5 | 28-28 | 2 | 53,778 | Ken Hill | Carlos Perez | Ken Hill | Carlos Perez | Troy Percival | 259 | 253 | 6 |
| 1999-06-07 | @ SFN | 57 | L 2-5 | 28-29 | 2 | 13,661 | Chuck Finley | Russ Ortiz | Russ Ortiz | Chuck Finley | Robb Nen | 261 | 258 | 3 |
| 1999-06-08 | @ SFN | 58 | L 2-6 | 28-30 | 2 | 11,721 | Steve Sparks | Shawn Estes | Shawn Estes | Steve Sparks | | 263 | 264 | -1 |
| 1999-06-09 | @ SFN | 59 | W 2-1 | 29-30 | 2 | 17,516 | Tim Belcher | Chris Brock | Tim Belcher | Chris Brock | Troy Percival | 265 | 265 | 0 |
| 1999-06-11 | vs ARI | 60 | L 2-12 | 30-30 | 2 | 37,042 | Ken Hill | Armando Reynoso | Armando Reynoso | Ken Hill | | 267 | 277 | -10 |
| 1999-06-12 | vs ARI | 61 | W 4-3 | 31-30 | 2 | 37,916 | Chuck Finley | Andy Benes | Mark Petkovsek | Andy Benes | Troy Percival | 271 | 280 | -9 |
| 1999-06-13 | vs ARI | 62 | L 1-3 | 31-31 | 2 | 29,176 | Omar Olivares | Omar Daal | Vladimir Nunez | Mark Petkovsek | Gregg Olson | 272 | 283 | -11 |
| 1999-06-15 | @ TOR | 63 | L 2-13 | 32-31 | 2 | 21,165 | Tim Belcher | David Wells | David Wells | Tim Belcher | | 274 | 296 | -22 |
| 1999-06-16 | @ TOR | 64 | L 2-3 | 32-32 | 2 | 22,184 | Steve Sparks | Joey Hamilton | Graeme Lloyd | Scott Schoeneweis | Billy Koch | 276 | 299 | -23 |
| 1999-06-17 | @ TOR | 65 | L 0-3 | 32-33 | 2 | 20,465 | Ken Hill | Kelvim Escobar | Kelvim Escobar | Ken Hill | Billy Koch | 276 | 302 | -26 |
| 1999-06-18 | @ NYA | 66 | L 1-4 | 32-34 | 2 | 39,996 | Chuck Finley | Andy Pettitte | Andy Pettitte | Chuck Finley | Mariano Rivera | 277 | 306 | -29 |
| 1999-06-19 | @ NYA | 67 | L 2-6 | 32-35 | 3 | 49,408 | Omar Olivares | Hideki Irabu | Hideki Irabu | Omar Olivares | Ramiro Mendoza | 279 | 312 | -33 |
| 1999-06-20 | @ NYA | 68 | W 4-2 | 33-35 | 3 | 55,626 | Tim Belcher | David Cone | Tim Belcher | David Cone | Troy Percival | 283 | 314 | -31 |
| 1999-06-22 | @ SEA | 69 | W 4-2 | 34-35 | 2 | 26,153 | Steve Sparks | Freddy Garcia | Mark Petkovsek | Freddy Garcia | Troy Percival | 287 | 316 | -29 |
| 1999-06-23 | @ SEA | 70 | L 3-8 | 34-36 | 3 | 25,087 | Ken Hill | John Halama | John Halama | Ken Hill | Frankie Rodriguez | 290 | 324 | -34 |
| 1999-06-24 | @ SEA | 71 | W 12-7 | 34-37 | 3 | 26,431 | Chuck Finley | Jeff Fassero | Scott Schoeneweis | Jose Mesa | Mark Petkovsek | 302 | 331 | -29 |
| 1999-06-25 | vs OAK | 72 | W 4-3 | 35-37 | 3 | 29,911 | Omar Olivares | Jimmy Haynes | Troy Percival | Doug Jones | | 306 | 334 | -28 |
| 1999-06-26 | vs OAK | 73 | W 5-4 | 36-37 | 3 | 29,957 | Tim Belcher | Gil Heredia | Mike Magnante | Brad Rigby | Troy Percival | 311 | 338 | -27 |
| 1999-06-27 | vs OAK | 74 | W 4-3 | 37-37 | 3 | 31,782 | Steve Sparks | Kenny Rogers | Steve Sparks | Kenny Rogers | Troy Percival | 315 | 341 | -26 |
| 1999-06-28 | vs TEX | 75 | L 1-9 | 37-38 | 3 | 20,539 | Chuck Finley | Mike Morgan | Mike Morgan | Chuck Finley | | 316 | 350 | -34 |
| 1999-06-29 | vs TEX | 76 | L 0-5 | 37-39 | 3 | 22,274 | Omar Olivares | John Burkett | John Burkett | Omar Olivares | | 316 | 355 | -39 |
| 1999-06-30 | vs TEX | 77 | L 4-18 | 38-39 | 3 | 23,450 | Ken Hill | Ryan Glynn | Ryan Glynn | Ken Hill | | 320 | 373 | -53 |
| 1999-07-02 | @ OAK | 78 | W 10-6 | 38-40 | 3 | 8,570 | Steve Sparks | Kenny Rogers | Mark Petkovsek | Chad Harville | | 330 | 379 | -49 |
| 1999-07-03 | @ OAK | 79 | L 7-9 | 38-41 | 3 | 50,916 | Chuck Finley | Gil Heredia | Gil Heredia | Chuck Finley | Billy Taylor | 337 | 388 | -51 |
| 1999-07-04 | @ OAK | 80 | W 5-2 | 39-41 | 3 | 19,721 | Omar Olivares | Mike Oquist | Omar Olivares | Mike Oquist | | 342 | 390 | -48 |
| 1999-07-05 | vs SEA | 81 | L 0-10 | 39-42 | 3 | 36,987 | Shigetoshi Hasegawa | Jeff Fassero | Jeff Fassero | Shigetoshi Hasegawa | | 342 | 400 | -58 |
| 1999-07-06 | vs SEA | 82 | W 8-2 | 40-42 | 3 | 22,444 | Mike Fyhrie | Gil Meche | Mark Petkovsek | Frankie Rodriguez | | 350 | 402 | -52 |
| 1999-07-07 | vs SEA | 83 | W 10-3 | 40-43 | 3 | 23,623 | Steve Sparks | Jamie Moyer | Steve Sparks | Jamie Moyer | | 360 | 405 | -45 |
| 1999-07-09 | @ COL | 84 | W 9-6 | 41-43 | 3 | 44,122 | Chuck Finley | Darryl Kile | Chuck Finley | Darryl Kile | Troy Percival | 369 | 411 | -42 |
| 1999-07-10 | @ COL | 85 | W 9-3 | 42-43 | 3 | 48,069 | Omar Olivares | Pedro Astacio | Omar Olivares | Pedro Astacio | | 378 | 414 | -36 |
| 1999-07-11 | @ COL | 86 | L 2-8 | 42-44 | 3 | 42,585 | Mike Fyhrie | Bobby Jones | Jerry DiPoto | Mike Fyhrie | | 380 | 422 | -42 |
| 1999-07-15 | vs LAN | 87 | W 7-6 | 43-44 | 3 | 43,911 | Chuck Finley | Kevin Brown | Mark Petkovsek | Alan Mills | | 387 | 428 | -41 |
| 1999-07-16 | vs LAN | 88 | L 1-3 | 43-45 | 3 | 43,727 | Omar Olivares | Ismael Valdez | Ismael Valdez | Omar Olivares | Jeff Shaw | 388 | 431 | -43 |
| 1999-07-17 | vs LAN | 89 | L 3-13 | 44-45 | 3 | 39,808 | Steve Sparks | Chan Ho Park | Chan Ho Park | Steve Sparks | | 391 | 444 | -53 |
| 1999-07-18 | vs SDN | 90 | L 3-6 | 44-46 | 3 | 37,697 | Mike Fyhrie | Brian Boehringer | Brian Boehringer | Mike Fyhrie | Trevor Hoffman | 394 | 450 | -56 |
| 1999-07-19 | vs SDN | 91 | L 1-4 | 44-47 | 3 | 25,217 | Ken Hill | Matt Clement | Dan Miceli | Shigetoshi Hasegawa | Trevor Hoffman | 395 | 454 | -59 |
| 1999-07-20 | vs SDN | 92 | L 1-2 | 44-48 | 3 | 35,247 | Chuck Finley | Andy Ashby | Andy Ashby | Mark Petkovsek | Trevor Hoffman | 396 | 456 | -60 |
| 1999-07-21 | @ TEX | 93 | L 5-9 | 44-49 | 3 | 35,849 | Omar Olivares | Aaron Sele | Aaron Sele | Omar Olivares | Jeff Zimmerman | 401 | 465 | -64 |
| 1999-07-22 | @ TEX | 94 | L 7-9 | 44-50 | 3 | 31,101 | Steve Sparks | John Burkett | John Burkett | Steve Sparks | Jeff Zimmerman | 408 | 474 | -66 |
| 1999-07-23 | @ BAL | 95 | L 0-1 | 44-51 | 3 | 43,945 | Jack McDowell | Juan Guzman | Juan Guzman | Jack McDowell | Mike Timlin | 408 | 475 | -67 |
| 1999-07-24 | @ BAL | 96 | L 4-8 | 44-52 | 3 | 48,544 | Ken Hill | Jason Johnson | Jason Johnson | Ken Hill | | 412 | 483 | -71 |
| 1999-07-25 | @ BAL | 97 | L 7-8 | 44-53 | 3 | 44,724 | Chuck Finley | Sidney Ponson | Scott Kamieniecki | Mike Holtz | | 419 | 491 | -72 |
| 1999-07-26 | @ TBA | 98 | L 0-7 | 44-54 | 3 | 15,596 | Omar Olivares | Bobby Witt | Bobby Witt | Omar Olivares | | 419 | 498 | -79 |
| 1999-07-27 | @ TBA | 99 | W 10-5 | 44-55 | 3 | 15,702 | Steve Sparks | Mickey Callaway | Mike Magnante | Mickey Callaway | | 429 | 503 | -74 |
| 1999-07-28 | @ TBA | 100 | L 1-4 | 44-56 | 3 | 18,336 | Jack McDowell | Ryan Rupe | Ryan Rupe | Jack McDowell | Roberto Hernandez | 430 | 507 | -77 |
| 1999-07-30 | vs MIN | 101 | L 1-3 | 44-57 | 4 | 38,319 | Ken Hill | Brad Radke | Brad Radke | Ken Hill | | 431 | 510 | -79 |
| 1999-07-31 | vs MIN | 102 | L 0-8 | 44-58 | 4 | 37,011 | Chuck Finley | Eric Milton | Eric Milton | Chuck Finley | | 431 | 518 | -87 |
| 1999-08-01 | vs MIN | 103 | W 2-1 | 45-58 | 4 | 24,045 | Steve Sparks | Joe Mays | Steve Sparks | Joe Mays | Troy Percival | 433 | 519 | -86 |
| 1999-08-02 | vs KCA | 104 | L 4-12 | 46-58 | 4 | 17,029 | Jack McDowell | Jose Rosado | Jose Rosado | Jack McDowell | | 437 | 531 | -94 |
| 1999-08-03 | vs KCA | 105 | L 0-7 | 46-59 | 4 | 18,454 | Mike Fyhrie | Jeff Suppan | Jeff Suppan | Mike Fyhrie | | 437 | 538 | -101 |
| 1999-08-04 | vs KCA | 106 | W 4-3 | 47-59 | 3 | 18,216 | Ken Hill | Jay Witasick | Ken Hill | Jay Witasick | Troy Percival | 441 | 541 | -100 |
| 1999-08-05 | vs BOS | 107 | W 8-0 | 48-59 | 3 | 26,175 | Chuck Finley | Brian Rose | Chuck Finley | Brian Rose | | 449 | 541 | -92 |
| 1999-08-06 | vs BOS | 108 | L 1-5 | 48-60 | 4 | 36,360 | Steve Sparks | Bret Saberhagen | Bret Saberhagen | Steve Sparks | | 450 | 546 | -96 |
| 1999-08-07 | vs BOS | 109 | L 3-14 | 49-60 | 4 | 36,577 | Tim Belcher | Pat Rapp | Pat Rapp | Tim Belcher | | 453 | 560 | -107 |
| 1999-08-08 | vs BOS | 110 | L 3-9 | 49-61 | 4 | 31,664 | Jack McDowell | Pedro Martinez | Pedro Martinez | Jack McDowell | | 456 | 569 | -113 |
| 1999-08-09 | vs CLE | 111 | L 0-4 | 49-62 | 4 | 22,013 | Ken Hill | Bartolo Colon | Bartolo Colon | Ken Hill | | 456 | 573 | -117 |
| 1999-08-10 | vs CLE | 112 | L 1-2 | 49-63 | 4 | 25,777 | Chuck Finley | Mark Langston | Ricardo Rincon | Mark Petkovsek | Michael Jackson | 457 | 575 | -118 |
| 1999-08-11 | vs CLE | 113 | L 3-4 | 49-64 | 4 | 26,399 | Steve Sparks | Dave Burba | Dave Burba | Steve Sparks | Michael Jackson | 460 | 579 | -119 |
| 1999-08-13 | @ DET | 114 | L 7-8 | 49-65 | 5 | 32,003 | Tim Belcher | Dave Borkowski | Todd Jones | Shigetoshi Hasegawa | | 467 | 587 | -120 |
| 1999-08-14 | @ DET | 115 | W 7-4 | 50-65 | 4 | 36,651 | Ken Hill | Brian Moehler | Mike Magnante | Brian Moehler | Troy Percival | 474 | 591 | -117 |
| 1999-08-15 | @ DET | 116 | W 10-2 | 50-66 | 4 | 34,237 | Chuck Finley | Justin Thompson | Chuck Finley | Justin Thompson | | 484 | 593 | -109 |
| 1999-08-16 | @ CHA | 117 | L 1-6 | 50-67 | 4 | 18,212 | Jarrod Washburn | Mike Sirotka | Mike Sirotka | Jarrod Washburn | | 485 | 599 | -114 |
| 1999-08-17 | @ CHA | 118 | L 3-4 | 50-68 | 4 | 14,943 | Steve Sparks | Jaime Navarro | Bob Howry | Mike Holtz | | 488 | 603 | -115 |
| 1999-08-18 | @ CHA | 119 | L 3-4 | 50-69 | 4 | 11,666 | Tim Belcher | James Baldwin | James Baldwin | Mike Magnante | Bob Howry | 491 | 607 | -116 |
| 1999-08-19 | @ CHA | 120 | W 9-2 | 51-69 | 4 | 14,171 | Ramon Ortiz | Jim Parque | Ramon Ortiz | Jim Parque | | 500 | 609 | -109 |
| 1999-08-20 | vs DET | 121 | W 5-1 | 52-69 | 4 | 29,910 | Chuck Finley | Brian Moehler | Chuck Finley | Brian Moehler | | 505 | 610 | -105 |
| 1999-08-21 | vs DET | 122 | L 0-5 | 52-70 | 4 | 28,575 | Jarrod Washburn | Jeff Weaver | Jeff Weaver | Jarrod Washburn | | 505 | 615 | -110 |
| 1999-08-22 | vs DET | 123 | L 3-12 | 53-70 | 4 | 24,465 | Steve Sparks | Dave Mlicki | Dave Mlicki | Steve Sparks | | 508 | 627 | -119 |
| 1999-08-23 | vs DET | 124 | W 6-5 | 54-70 | 4 | 17,145 | Tim Belcher | Dave Borkowski | Troy Percival | Doug Brocail | | 514 | 632 | -118 |
| 1999-08-24 | vs TOR | 125 | L 1-5 | 54-71 | 4 | 21,492 | Ramon Ortiz | Pat Hentgen | Pat Hentgen | Ramon Ortiz | Billy Koch | 515 | 637 | -122 |
| 1999-08-25 | vs TOR | 126 | L 2-7 | 54-72 | 4 | 21,592 | Chuck Finley | Joey Hamilton | Joey Hamilton | Chuck Finley | | 517 | 644 | -127 |
| 1999-08-27 | @ BOS | 127 | L 3-4 | 54-73 | 4 | 32,921 | Jarrod Washburn | Kent Mercker | Rich Garces | Troy Percival | Derek Lowe | 520 | 648 | -128 |
| 1999-08-28 | @ BOS | 128 | L 6-7 | 54-74 | 4 | 33,060 | Steve Sparks | Tim Wakefield | Derek Lowe | Lou Pote | | 526 | 655 | -129 |
| 1999-08-29 | @ BOS | 129 | L 4-7 | 54-75 | 4 | 32,253 | Tim Belcher | Pat Rapp | Pat Rapp | Tim Belcher | Derek Lowe | 530 | 662 | -132 |
| 1999-08-30 | @ CLE | 130 | L 5-7 | 54-76 | 5 | 43,295 | Ramon Ortiz | Bartolo Colon | Bartolo Colon | Al Levine | Michael Jackson | 535 | 669 | -134 |
| 1999-08-31 | @ CLE | 131 | L 12-14 | 54-77 | 4 | 43,284 | Chuck Finley | Dwight Gooden | Jim Poole | Troy Percival | Paul Shuey | 547 | 683 | -136 |
| 1999-09-01 | @ CLE | 132 | L 1-8 | 54-78 | 4 | 43,399 | Jarrod Washburn | Dave Burba | Dave Burba | Jarrod Washburn | | 548 | 691 | -143 |
| 1999-09-02 | @ CLE | 133 | L 5-6 | 54-79 | 4 | 43,369 | Steve Sparks | Charles Nagy | Charles Nagy | Steve Sparks | Michael Jackson | 553 | 697 | -144 |
| 1999-09-03 | vs NYA | 134 | W 8-2 | 55-79 | 4 | 35,782 | Tim Belcher | Andy Pettitte | Tim Belcher | Andy Pettitte | | 561 | 699 | -138 |
| 1999-09-04 | vs NYA | 135 | L 6-9 | 55-80 | 4 | 30,589 | Ramon Ortiz | Hideki Irabu | Allen Watson | Juan Alvarez | Mariano Rivera | 567 | 708 | -141 |
| 1999-09-05 | vs NYA | 136 | L 3-8 | 55-81 | 4 | 35,481 | Mike Fyhrie | Ed Yarnall | Ed Yarnall | Mike Fyhrie | | 570 | 716 | -146 |
| 1999-09-06 | vs NYA | 137 | W 5-3 | 56-81 | 5 | 31,749 | Jarrod Washburn | Roger Clemens | Jarrod Washburn | Roger Clemens | Troy Percival | 575 | 719 | -144 |
| 1999-09-07 | vs CHA | 138 | W 14-1 | 57-81 | 4 | 16,867 | Brian Cooper | Mike Sirotka | Brian Cooper | Mike Sirotka | | 589 | 720 | -131 |
| 1999-09-08 | vs CHA | 139 | W 6-5 | 58-81 | 4 | 17,246 | Tim Belcher | James Baldwin | Troy Percival | Bill Simas | | 595 | 725 | -130 |
| 1999-09-10 | @ MIN | 140 | W 4-2 | 59-81 | 4 | 11,200 | Chuck Finley | Brad Radke | Chuck Finley | Brad Radke | Troy Percival | 599 | 727 | -128 |
| 1999-09-11 | @ MIN | 141 | L 0-7 | 59-82 | 4 | 11,222 | Ramon Ortiz | Eric Milton | Eric Milton | Ramon Ortiz | | 599 | 734 | -135 |
| 1999-09-12 | @ MIN | 142 | W 6-3 | 60-82 | 4 | 11,301 | Jarrod Washburn | Joe Mays | Jarrod Washburn | Joe Mays | | 605 | 737 | -132 |
| 1999-09-13 | @ MIN | 143 | W 6-5 | 61-82 | 4 | 8,716 | Brian Cooper | LaTroy Hawkins | Mike Magnante | LaTroy Hawkins | Shigetoshi Hasegawa | 611 | 742 | -131 |
| 1999-09-14 | @ KCA | 144 | W 8-6 | 62-82 | 5 | 0 | Tim Belcher | Mac Suzuki | Lou Pote | Alvin Morman | Shigetoshi Hasegawa | 619 | 748 | -129 |
| 1999-09-14 | @ KCA | 145 | W 6-5 | 62-82 | 5 | 11,290 | Mike Fyhrie | Chris Fussell | Shigetoshi Hasegawa | Tim Byrdak | Troy Percival | 625 | 753 | -128 |
| 1999-09-15 | @ KCA | 146 | W 1-0 | 64-82 | 4 | 10,781 | Chuck Finley | Blake Stein | Chuck Finley | Lance Carter | Troy Percival | 626 | 753 | -127 |
| 1999-09-16 | @ KCA | 147 | L 1-7 | 64-83 | 4 | 11,602 | Ramon Ortiz | Jeff Suppan | Jeff Suppan | Ramon Ortiz | | 627 | 760 | -133 |
| 1999-09-17 | vs BAL | 148 | L 2-4 | 64-84 | 4 | 28,865 | Jarrod Washburn | Scott Erickson | Scott Erickson | Jarrod Washburn | Mike Timlin | 629 | 764 | -135 |
| 1999-09-18 | vs BAL | 149 | L 3-6 | 64-85 | 4 | 36,531 | Brian Cooper | Sidney Ponson | Sidney Ponson | Brian Cooper | Mike Timlin | 632 | 770 | -138 |
| 1999-09-19 | vs BAL | 150 | L 4-5 | 64-86 | 4 | 22,526 | Mike Fyhrie | Mike Mussina | Gabe Molina | Troy Percival | Mike Timlin | 636 | 775 | -139 |
| 1999-09-20 | vs TBA | 151 | W 10-5 | 64-87 | 4 | 16,165 | Chuck Finley | Wilson Alvarez | Chuck Finley | Wilson Alvarez | | 646 | 780 | -134 |
| 1999-09-21 | vs TBA | 152 | W 7-5 | 65-87 | 4 | 16,486 | Ramon Ortiz | Dave Eiland | Ramon Ortiz | Dave Eiland | Troy Percival | 653 | 785 | -132 |
| 1999-09-22 | vs TBA | 153 | W 8-5 | 66-87 | 4 | 16,801 | Jarrod Washburn | Dan Wheeler | Jarrod Washburn | Dan Wheeler | | 661 | 790 | -129 |
| 1999-09-24 | @ SEA | 154 | L 3-4 | 66-88 | 4 | 44,403 | Brian Cooper | Gil Meche | Jose Mesa | Troy Percival | | 664 | 794 | -130 |
| 1999-09-25 | @ SEA | 155 | W 7-3 | 67-88 | 4 | 44,308 | Chuck Finley | Jamie Moyer | Chuck Finley | Jamie Moyer | | 671 | 797 | -126 |
| 1999-09-26 | @ SEA | 156 | L 2-3 | 67-89 | 4 | 44,485 | Ramon Ortiz | Robert Ramsay | Tom Davey | Shigetoshi Hasegawa | | 673 | 800 | -127 |
| 1999-09-28 | vs OAK | 157 | L 3-9 | 67-90 | 4 | 17,981 | Jarrod Washburn | Tim Hudson | Tim Hudson | Jarrod Washburn | Ron Mahay | 676 | 809 | -133 |
| 1999-09-29 | vs OAK | 158 | W 7-4 | 68-90 | 4 | 17,596 | Brian Cooper | Omar Olivares | Shigetoshi Hasegawa | T.J. Mathews | Lou Pote | 683 | 813 | -130 |
| 1999-09-30 | vs OAK | 159 | W 5-4 | 69-90 | 4 | 19,567 | Chuck Finley | Gil Heredia | Mark Petkovsek | Jason Isringhausen | Lou Pote | 688 | 817 | -129 |
| 1999-10-01 | vs TEX | 160 | W 7-6 | 70-90 | 4 | 25,515 | Ramon Ortiz | Esteban Loaiza | Mike Holtz | Mike Morgan | | 695 | 823 | -128 |
| 1999-10-02 | vs TEX | 161 | W 15-3 | 70-91 | 4 | 33,239 | Al Levine | Rick Helling | Shigetoshi Hasegawa | Rick Helling | | 710 | 826 | -116 |
| 1999-10-03 | vs TEX | 162 | W 1-0 | 71-91 | 4 | 23,556 | Jarrod Washburn | Matt Perisho | Jarrod Washburn | Mike Morgan | Lou Pote | 711 | 826 | -115 |