| Week 1 (10/14/2019) | Eagles Norfolk Anderson vs Eagles Norfolk Miller |
| Week 1 (10/14/2019) | The O Lounge Hoskinson vs Jake's Bar Allegedly @ Harbor |
| Week 2 (10/21/2019) | Jake's Bar Allegedly vs Eagles Norfolk Anderson |
| Week 2 (10/21/2019) | Eagles Norfolk Miller vs The O Lounge Runnin' Rebs |
| Week 3 (10/28/2019) | The O Lounge Hoskinson vs The O Lounge Runnin' Rebs |
| Week 3 (10/28/2019) | Eagles Norfolk Miller vs Jake's Bar Allegedly |
| Week 4 (11/4/2019) | The O Lounge Runnin' Rebs vs Jake's Bar Allegedly |
| Week 4 (11/4/2019) | Eagles Norfolk Anderson vs The O Lounge Hoskinson |
| Week 5 (11/11/2019) | Eagles Norfolk Anderson vs The O Lounge Runnin' Rebs |
| Week 5 (11/11/2019) | The O Lounge Hoskinson vs Eagles Norfolk Miller |
| Week 6 (11/18/2019) | Jake's Bar Allegedly vs The O Lounge Hoskinson |
| Week 6 (11/18/2019) | Eagles Norfolk Miller vs Eagles Norfolk Anderson |
| Week 7 (11/25/2019) | The O Lounge Runnin' Rebs vs Eagles Norfolk Miller |
| Week 7 (11/25/2019) | Eagles Norfolk Anderson vs Jake's Bar Allegedly |
| Week 8 (12/2/2019) | The O Lounge Runnin' Rebs vs The O Lounge Hoskinson |
| Week 8 (12/2/2019) | Jake's Bar Allegedly vs Eagles Norfolk Miller |
| Week 9 (12/9/2019) | Jake's Bar Allegedly vs The O Lounge Runnin' Rebs |
| Week 9 (12/9/2019) | The O Lounge Hoskinson vs Eagles Norfolk Anderson |
| Week 10 (12/16/2019) | The O Lounge Runnin' Rebs vs Eagles Norfolk Anderson |
| Week 10 (12/16/2019) | Eagles Norfolk Miller vs The O Lounge Hoskinson |
| Week of 12/23/2019 | No Leagues - Happy Holidays |
| Week of 12/30/2019 | No Leagues - Happy Holidays |
| Week 11 (1/6/2020) | Eagles Norfolk Anderson vs Eagles Norfolk Miller |
| Week 11 (1/6/2020) | The O Lounge Hoskinson vs Jake's Bar Allegedly |
| Week 12 (1/13/2020) | Jake's Bar Allegedly vs Eagles Norfolk Anderson |
| Week 12 (1/13/2020) | Eagles Norfolk Miller vs The O Lounge Runnin' Rebs |
| Week 13 (1/20/2020) | The O Lounge Hoskinson vs The O Lounge Runnin' Rebs |
| Week 13 (1/20/2020) | Eagles Norfolk Miller vs Jake's Bar Allegedly |
| Week 14 (1/27/2020) | The O Lounge Runnin' Rebs vs Jake's Bar Allegedly |
| Week 14 (1/27/2020) | Eagles Norfolk Anderson vs The O Lounge Hoskinson |
| Week 15 (2/3/2020) | Eagles Norfolk Anderson vs The O Lounge Runnin' Rebs |
| Week 15 (2/3/2020) | The O Lounge Hoskinson vs Eagles Norfolk Miller |