| Dominican Summer League | 2023/07/25 15:00 | DSL Pirates Black v DSL Cubs Blue | L | 5-7 |
| Dominican Summer League | 2023/07/24 15:00 | DSL Cubs Blue v DSL Pirates Black | L | 7-1 |
| Dominican Summer League | 2023/07/18 15:00 | DSL Pirates Black v DSL Cubs Blue | W | 6-5 |
| Dominican Summer League | 2023/07/08 14:30 | DSL Cubs Blue v DSL Pirates Black | W | 1-7 |
| Dominican Summer League | 2023/06/13 15:00 | DSL Cubs Blue v DSL Pirates Black | W | 1-3 |
| Dominican Summer League | 2023/06/12 15:00 | DSL Pirates Black v DSL Cubs Blue | W | 7-3 |
| Dominican Summer League | 2022/08/06 15:00 | DSL Cubs Blue v DSL Pirates Black | L | 4-2 |
| Dominican Summer League | 2022/07/09 15:00 | DSL Cubs Blue v DSL Pirates Black | L | 2-0 |
| Dominican Summer League | 2023/08/19 15:00 | DSL Pirates Black v DSL Cubs Red | L | 4-9 |
| Dominican Summer League | 2023/08/18 15:00 | DSL Red Sox Red v DSL Pirates Black | L | 6-3 |
| Dominican Summer League | 2023/08/17 14:35 | DSL Tigers v DSL Pirates Black | L | 4-2 |
| Dominican Summer League | 2023/08/15 15:00 | DSL Pirates Black v DSL Cubs Red | W | 7-3 |
| Dominican Summer League | 2023/08/14 15:00 | DSL Pirates Black v DSL Mariners | L | 3-10 |
| Dominican Summer League | 2023/08/12 15:00 | DSL Tigers 2 v DSL Pirates Black | L | 13-6 |
| Dominican Summer League | 2023/08/11 15:00 | DSL Pirates Black v DSL Pirates Gold | L | 1-7 |
| Dominican Summer League | 2023/08/10 15:00 | DSL Mets Orange v DSL Pirates Black | L | 15-7 |
| Dominican Summer League | 2023/08/21 14:30 | DSL Red Sox Blue v DSL Cubs Blue | W | 3-6 |
| Dominican Summer League | 2023/08/19 15:00 | DSL Cubs Blue v DSL Giants Black | L | 3-4 |
| Dominican Summer League | 2023/08/17 14:30 | DSL Orioles Orange v DSL Cubs Blue | L | 4-3 |
| Dominican Summer League | 2023/08/15 14:30 | DSL Cubs Blue v DSL Red Sox Blue | L | 4-10 |
| Dominican Summer League | 2023/08/14 15:00 | DSL Cubs Blue v DSL Tigers 2 | L | 4-5 |
| Dominican Summer League | 2023/08/12 15:00 | DSL Pirates Gold v DSL Cubs Blue | L | 8-3 |
| Dominican Summer League | 2023/08/10 15:00 | DSL Red Sox Red v DSL Cubs Blue | L | 3-0 |
| Dominican Summer League | 2023/08/08 14:00 | DSL Cubs Blue v DSL Cubs Red | L | 1-2 |