| Month | Game | Strat Date | + | Away | Pitcher | Balance | At | Home | Pitcher | Balance |
| May | 1 | 5/12/2025 | CHI | Spencer Schwellenbach | 3R | At | NYY | Jack Leiter | 5L | |
| May | 2 | 5/13/2025 | CHI | Nick Martinez | 2L | At | NYY | Ranger Suarez* | 2L | |
| May | 3 | 5/14/2025 | CHI | Noah Cameron* | 2L | At | NYY | Luis Castillo | 6R | |
| May | OFF | 5/15/2025 | ||||||||
| May | 4 | 5/16/2025 | TEX | Nick Lodolo* | 5R | At | CHI | Dean Kremer | 1R | |
| May | 5 | 5/17/2025 | TEX | Hunter Brown | E | At | CHI | Spencer Schwellenbach | 3R | |
| May | 6 | 5/18/2025 | TEX | Bailey Ober | 1L | At | CHI | Nick Martinez | 2L | |
| May | 7 | 5/19/2025 | CHI | Randy Vasquez | 2R | At | CRC | Garrett Crochet* | 5L | |
| May | 8 | 5/20/2025 | CHI | Noah Cameron* | 2L | At | CRC | Kevin Gausman | 3L | |
| May | 9 | 5/21/2025 | CHI | Dean Kremer | 1R | At | CRC | Tanner Bibee | 1L | |
| May | 10 | 5/22/2025 | HUC | Chris Bassitt | 4R | At | CHI | Spencer Schwellenbach | 3R | |
| May | 11 | 5/23/2025 | HUC | Drew Rasmussen | 3R | At | CHI | Nick Martinez | 2L | |
| May | 12 | 5/24/2025 | HUC | Reese Olson | 3L | At | CHI | Randy Vasquez | 2R | |
| May | OFF | 5/25/2025 | ||||||||
| May | 13 | 5/26/2025 | + | TAM | Cam Schlittler | 1L | At | CHI | Dean Kremer | 1R |
| May | 14 | 5/27/2025 | + | TAM | Brayan Bello | E | At | CHI | Noah Cameron* | 2L |
| May | 15 | 5/28/2025 | + | TAM | Griffin Canning | E | At | CHI | Spencer Schwellenbach | 3R |
| May | 16 | 5/29/2025 | + | TAM | Michael King | 1R | At | CHI | Randy Vasquez | 2R |
| May | 17 | 5/30/2025 | + | TAM | Trevor Rogers* | 1L | At | CHI | Nick Martinez | 2L |
| May | 18 | 5/31/2025 | + | CHI | Dean Kremer | 1R | At | SRD | Taj Bradley | 1R |
| May | 19 | 6/1/2025 | + | CHI | Noah Cameron* | 2L | At | SRD | Kyle Freeland* | 3L |
| May | 20 | 6/2/2025 | + | CHI | Spencer Schwellenbach | 3R | At | SRD | Robbie Ray* | 3L |
| May | 21 | 6/3/2025 | + | CHI | Randy Vasquez | 2R | At | SRD | Chris Sale* | 3L |
| May | OFF | 6/4/2025 | ||||||||
| May | 22 | 6/5/2025 | NIM | Jeffrey Springs* | 1L | At | CHI | Dean Kremer | 1R | |
| May | 23 | 6/6/2025 | NIM | Jameson Taillon | 7L | At | CHI | Nick Martinez | 2L | |
| May | 24 | 6/7/2025 | NIM | Matt Boyd* | 3L | At | CHI | Noah Cameron* | 2L | |
| + Indicates In Division Game | ||||||||||