| Week 1 (9/22/2019) | Chug A Lug Team 2 vs Otherside Team 1 |
| Week 1 (9/22/2019) | Otherside Team 4 vs Chug A Lug Team 5 |
| Week 2 (9/29/2019) | Otherside Team 3 vs Otherside Team 4 @ Chug A Lug |
| Week 2 (9/29/2019) | Chug A Lug Team 5 vs Chug A Lug Team 2 @ Otherside |
| Week 3 (10/6/2019) | Otherside Team 4 vs Otherside Team 1 @ Chug A Lug |
| Week 3 (10/6/2019) | Chug A Lug Team 5 vs Otherside Team 3 @ Otherside |
| Week 4 (10/13/2019) | Otherside Team 1 vs Chug A Lug Team 5 |
| Week 4 (10/13/2019) | Chug A Lug Team 2 vs Otherside Team 3 |
| Week 5 (10/20/2019) | Otherside Team 3 vs Otherside Team 1 @ Chug A Lug |
| Week 5 (10/20/2019) | Otherside Team 4 vs Chug A Lug Team 2 |
| Week 6 (10/27/2019) | Otherside Team 1 vs Chug A Lug Team 2 @ Chug A Lug |
| Week 6 (10/27/2019) | Chug A Lug Team 5 vs Otherside Team 4 @ Otherside |
| Week of 11/3/2019 | No Leagues - Jerrry Siefken Memorial Tournament |
| Week 7 (11/10/2019) | Chug A Lug Team 2 vs Chug A Lug Team 5 |
| Week 7 (11/10/2019) | Otherside Team 4 vs Otherside Team 3 |
| Week 8 (11/17/2019) | Otherside Team 1 vs Otherside Team 4 |
| Week 8 (11/17/2019) | Otherside Team 3 vs Chug A Lug Team 5 @ Chug A Lug |
| Week 9 (11/24/2019) | Otherside Team 3 vs Chug A Lug Team 2 @ Chug A Lug |
| Week 9 (11/24/2019) | Chug A Lug Team 5 vs Otherside Team 1 @ Otherside |
| Week of 12/1/2019 | No Leagues - Thanksgiving |
| Week 10 (12/8/2019) | Otherside Team 1 vs Otherside Team 3 @ Chug A Lug |
| Week 10 (12/8/2019) | Chug A Lug Team 2 vs Otherside Team 4 @ Otherside |
| Week 11 (12/15/2019) | Chug A Lug Team 2 vs Otherside Team 1 |
| Week 11 (12/15/2019) | Otherside Team 4 vs Chug A Lug Team 5 |
| Week 12 (12/22/2019) | Otherside Team 3 vs Otherside Team 4 @ Chug A Lug |
| Week 12 (12/22/2019) | Chug A Lug Team 5 vs Chug A Lug Team 2 @ Otherside |
| Week of 12/29/2019 | No Leagues - Christmas and New Years |
| Week of 1/5/2020 | No Leagues - Holidays |
| Week of 1/12/2020 | No Leagues - Heartland Tournament - Columbus |
| Week 13 (1/19/2020) | Otherside Team 4 vs Otherside Team 1 @ Chug A Lug |
| Week 13 (1/19/2020) | Chug A Lug Team 5 vs Otherside Team 3 @ Otherside |
| Week 14 (1/26/2020) | Otherside Team 1 vs Chug A Lug Team 5 |
| Week 14 (1/26/2020) | Chug A Lug Team 2 vs Otherside Team 3 |
| Week 15 (2/2/2020) | Otherside Team 3 vs Otherside Team 1 @ Chug A Lug |
| Week 15 (2/2/2020) | Otherside Team 4 vs Chug A Lug Team 2 |
| Week 16 (2/9/2020) | Otherside Team 1 vs Chug A Lug Team 2 @ Chug A Lug |
| Week 16 (2/9/2020) | Chug A Lug Team 5 vs Otherside Team 4 @ Otherside |
| Week 17 (2/16/2020) | Chug A Lug Team 2 vs Chug A Lug Team 5 |
| Week 17 (2/16/2020) | Otherside Team 4 vs Otherside Team 3 |
| Week 18 (2/23/2020) | Otherside Team 1 vs Otherside Team 4 |
| Week 18 (2/23/2020) | Otherside Team 3 vs Chug A Lug Team 5 @ Chug A Lug |
| Week 19 (3/1/2020) | Otherside Team 3 vs Chug A Lug Team 2 @ Chug A Lug |
| Week 19 (3/1/2020) | Chug A Lug Team 5 vs Otherside Team 1 @ Otherside |
| Week 20 (3/8/2020) | Otherside Team 1 vs Otherside Team 3 |
| Week 20 (3/8/2020) | Chug A Lug Team 2 vs Otherside Team 4 |
| Week 21 (3/15/2020) | Chug A Lug Team 2 vs Otherside Team 1 |
| Week 21 (3/15/2020) | Otherside Team 4 vs Chug A Lug Team 5 |