| Month | Game | Strat Date | + | Away | Pitcher | Balance | At | Home | Pitcher | Balance |
| September | 1 | 8/31/2023 | CHI | Andre Jackson | 4L | At | WRK | Joe Musgrove | 7L | |
| September | 2 | 9/1/2023 | CHI | Fernando Cruz | 1R | At | WRK | Alex Faedo | 6L | |
| September | 3 | 9/2/2023 | CHI | Randy Vasquez | E | At | WRK | Julio Urias* | 3L | |
| September | 4 | 9/3/2023 | DUB | Nestor Cortes* | 9L | At | CHI | Kyle Gibson | 3R | |
| September | 5 | 9/4/2023 | DUB | Kyle Freeland* | 6L | At | CHI | Jordan Lyles | 1L | |
| September | 6 | 9/5/2023 | DUB | Carlos Rodon* | 5L | At | CHI | Andre Jackson | 4L | |
| September | OFF | 9/6/2023 | ||||||||
| September | 7 | 9/7/2023 | + | SRD | Alex Wood* | 2L | At | CHI | Wade Miley* | 2L |
| September | 8 | 9/8/2023 | + | SRD | Chase Anderson | 1L | At | CHI | Kyle Gibson | 3R |
| September | 9 | 9/9/2023 | + | SRD | Chris Sale* | 1L | At | CHI | Jordan Lyles | 1L |
| September | 10 | 9/10/2023 | + | SRD | Dakota Hudson | 2R | At | CHI | Andre Jackson | 4L |
| September | 11 | 9/11/2023 | + | SRD | Cal Quantrill | 2R | At | CHI | Aaron Civale | E |
| September | 12 | 9/12/2023 | + | CHI | Wade Miley* | 2L | At | DYE | Aaron Nola | 1R |
| September | 13 | 9/13/2023 | + | CHI | Kyle Gibson | 3R | At | DYE | Ryan Pepiot | 1L |
| September | 14 | 9/14/2023 | + | CHI | Jordan Lyles | 1L | At | DYE | George Kirby | E |
| September | 15 | 9/15/2023 | + | CHI | Andre Jackson | 4L | At | DYE | Kyle Hendricks | 5L |
| September | OFF | 9/16/2023 | ||||||||
| September | 16 | 9/17/2023 | + | CHI | Aaron Civale | E | At | TAM | Johan Oviedo | 2R |
| September | 17 | 9/18/2023 | + | CHI | Kyle Gibson | 3R | At | TAM | Tyler Wells | 4L |
| September | 18 | 9/19/2023 | + | CHI | Jordan Lyles | 1L | At | TAM | Touki Toussaint | 2L |
| September | 19 | 9/20/2023 | + | CHI | Andre Jackson | 4L | At | TAM | Michael King | 6L |
| September | 20 | 9/21/2023 | + | CHI | Wade Miley* | 2L | At | TAM | Tyler Glasnow | 6R |
| September | 21 | 9/22/2023 | + | DYE | Ryan Pepiot | 1L | At | CHI | Aaron Civale | E |
| September | 22 | 9/23/2023 | + | DYE | Miles Mikolas | 2R | At | CHI | Kyle Gibson | 3R |
| September | 23 | 9/24/2023 | + | DYE | George Kirby | E | At | CHI | Jordan Lyles | 1L |
| September | 24 | 9/25/2023 | + | DYE | Aaron Nola | 1R | At | CHI | Andre Jackson | 4L |
| + Indicates In Division Game | ||||||||||