| Week 1 (3/21/2023) | Grant Street Outta Shape vs Bogie's Clocked In |
| Week 1 (3/21/2023) | Papa Chuck's Team Bartles vs Musette Bar 8 Balls of Fire @ Shooters |
| Week 1 (3/21/2023) | Musette Bar Team McSorley vs Musette Bar Team Uday |
| Week 1 (3/21/2023) | Shooters Team Polito vs Papa Chuck's Team Kashe |
| Week 1 (3/21/2023) | Musette Bar Ginger Kale vs Shooters Team Stuart |
| Week 2 (3/28/2023) | Grant Street Outta Shape vs Shooters Team Stuart |
| Week 2 (3/28/2023) | Musette Bar 8 Balls of Fire vs Musette Bar Team McSorley |
| Week 2 (3/28/2023) | Bogie's Clocked In vs Papa Chuck's Team Bartles |
| Week 2 (3/28/2023) | Papa Chuck's Team Kashe vs Musette Bar Ginger Kale @ Shooters |
| Week 2 (3/28/2023) | Musette Bar Team Uday vs Shooters Team Polito |
| Week 3 (4/4/2023) | Papa Chuck's Team Bartles vs Grant Street Outta Shape @ Shooters |
| Week 3 (4/4/2023) | Musette Bar Team McSorley vs Bogie's Clocked In |
| Week 3 (4/4/2023) | Shooters Team Polito vs Musette Bar 8 Balls of Fire |
| Week 3 (4/4/2023) | Musette Bar Ginger Kale vs Musette Bar Team Uday |
| Week 3 (4/4/2023) | Shooters Team Stuart vs Papa Chuck's Team Kashe |
| Week 4 (4/11/2023) | Grant Street Outta Shape vs Papa Chuck's Team Kashe |
| Week 4 (4/11/2023) | Papa Chuck's Team Bartles vs Musette Bar Team McSorley @ Shooters |
| Week 4 (4/11/2023) | Musette Bar 8 Balls of Fire vs Musette Bar Ginger Kale |
| Week 4 (4/11/2023) | Bogie's Clocked In vs Shooters Team Polito |
| Week 4 (4/11/2023) | Musette Bar Team Uday vs Shooters Team Stuart |
| Week 5 (4/18/2023) | Musette Bar Team McSorley vs Grant Street Outta Shape |
| Week 5 (4/18/2023) | Papa Chuck's Team Kashe vs Musette Bar Team Uday @ Shooters |
| Week 5 (4/18/2023) | Shooters Team Polito vs Papa Chuck's Team Bartles |
| Week 5 (4/18/2023) | Musette Bar Ginger Kale vs Bogie's Clocked In |
| Week 5 (4/18/2023) | Shooters Team Stuart vs Musette Bar 8 Balls of Fire |
| Week 6 (4/25/2023) | Grant Street Outta Shape vs Musette Bar Team Uday |
| Week 6 (4/25/2023) | Papa Chuck's Team Bartles vs Musette Bar Ginger Kale @ Shooters |
| Week 6 (4/25/2023) | Musette Bar 8 Balls of Fire vs Papa Chuck's Team Kashe |
| Week 6 (4/25/2023) | Bogie's Clocked In vs Shooters Team Stuart |
| Week 6 (4/25/2023) | Musette Bar Team McSorley vs Shooters Team Polito |
| Week 7 (5/2/2023) | Papa Chuck's Team Kashe vs Bogie's Clocked In @ Shooters |
| Week 7 (5/2/2023) | Shooters Team Polito vs Grant Street Outta Shape |
| Week 7 (5/2/2023) | Musette Bar Team Uday vs Musette Bar 8 Balls of Fire |
| Week 7 (5/2/2023) | Musette Bar Ginger Kale vs Musette Bar Team McSorley |
| Week 7 (5/2/2023) | Shooters Team Stuart vs Papa Chuck's Team Bartles |
| Week 8 (5/9/2023) | Grant Street Outta Shape vs Musette Bar 8 Balls of Fire |
| Week 8 (5/9/2023) | Papa Chuck's Team Bartles vs Papa Chuck's Team Kashe @ Shooters |
| Week 8 (5/9/2023) | Bogie's Clocked In vs Musette Bar Team Uday |
| Week 8 (5/9/2023) | Musette Bar Team McSorley vs Shooters Team Stuart |
| Week 8 (5/9/2023) | Shooters Team Polito vs Musette Bar Ginger Kale |
| Week 9 (5/16/2023) | Musette Bar 8 Balls of Fire vs Bogie's Clocked In |
| Week 9 (5/16/2023) | Papa Chuck's Team Kashe vs Musette Bar Team McSorley @ Shooters |
| Week 9 (5/16/2023) | Musette Bar Team Uday vs Papa Chuck's Team Bartles |
| Week 9 (5/16/2023) | Musette Bar Ginger Kale vs Grant Street Outta Shape |
| Week 9 (5/16/2023) | Shooters Team Stuart vs Shooters Team Polito |
| Week 10 (5/23/2023) | Musette Bar 8 Balls of Fire vs Shooters Team Polito |
| Week 10 (5/23/2023) | Musette Bar Team McSorley vs Grant Street Outta Shape |
| Week 10 (5/23/2023) | Papa Chuck's Team Kashe vs Bogie's Clocked In |
| Week 10 (5/23/2023) | Musette Bar Team Uday vs Musette Bar Ginger Kale |
| Week 10 (5/23/2023) | Shooters Team Stuart vs Papa Chuck's Team Bartles |