| Week 1 (9/15/2019) | CJ's It's Miller Time vs 1st Avenue No Names |
| Week 1 (9/15/2019) | Rosie's South Raptors vs Sportscasters Lost Cause |
| Week 1 (9/15/2019) | 1st Avenue P V K vs Risky's Rollin' Nerdy |
| Week 2 (9/22/2019) | Sportscasters Lost Cause vs CJ's It's Miller Time |
| Week 2 (9/22/2019) | Madsen's The Leftovers vs 1st Avenue P V K |
| Week 2 (9/22/2019) | Risky's Rollin' Nerdy vs Rosie's South Raptors |
| Week 3 (9/29/2019) | CJ's It's Miller Time vs Madsen's The Leftovers |
| Week 3 (9/29/2019) | Rosie's South Raptors vs 1st Avenue No Names |
| Week 3 (9/29/2019) | 1st Avenue P V K vs Sportscasters Lost Cause |
| Week 4 (10/6/2019) | 1st Avenue No Names vs 1st Avenue P V K |
| Week 4 (10/6/2019) | Madsen's The Leftovers vs Rosie's South Raptors |
| Week 4 (10/6/2019) | Risky's Rollin' Nerdy vs CJ's It's Miller Time |
| Week 5 (10/13/2019) | CJ's It's Miller Time vs Rosie's South Raptors |
| Week 5 (10/13/2019) | 1st Avenue No Names vs Sportscasters Lost Cause |
| Week 5 (10/13/2019) | Madsen's The Leftovers vs Risky's Rollin' Nerdy |
| Week 6 (10/20/2019) | Sportscasters Lost Cause vs Madsen's The Leftovers |
| Week 6 (10/20/2019) | 1st Avenue P V K vs CJ's It's Miller Time |
| Week 6 (10/20/2019) | Risky's Rollin' Nerdy vs 1st Avenue No Names |
| Week 7 (10/27/2019) | 1st Avenue No Names vs Madsen's The Leftovers |
| Week 7 (10/27/2019) | Rosie's South Raptors vs 1st Avenue P V K |
| Week 7 (10/27/2019) | Sportscasters Lost Cause vs Risky's Rollin' Nerdy |
| Week 8 (11/3/2019) | 1st Avenue No Names vs CJ's It's Miller Time |
| Week 8 (11/3/2019) | Sportscasters Lost Cause vs Rosie's South Raptors |
| Week 8 (11/3/2019) | Risky's Rollin' Nerdy vs 1st Avenue P V K |
| Week 9 (11/10/2019) | CJ's It's Miller Time vs Sportscasters Lost Cause |
| Week 9 (11/10/2019) | Rosie's South Raptors vs Risky's Rollin' Nerdy @ Risky's |
| Week 9 (11/10/2019) | 1st Avenue P V K vs Madsen's The Leftovers |
| Week 10 (11/17/2019) | 1st Avenue No Names vs Rosie's South Raptors |
| Week 10 (11/17/2019) | Sportscasters Lost Cause vs 1st Avenue P V K |
| Week 10 (11/17/2019) | Madsen's The Leftovers vs CJ's It's Miller Time |
| Week 11 (11/24/2019) | CJ's It's Miller Time vs Risky's Rollin' Nerdy |
| Week 11 (11/24/2019) | Rosie's South Raptors vs Madsen's The Leftovers |
| Week 11 (11/24/2019) | 1st Avenue P V K vs 1st Avenue No Names |
| Week of 12/1/2019 | No Leagues - Happy Thanksgiving! |
| Week 12 (12/8/2019) | Rosie's South Raptors vs CJ's It's Miller Time |
| Week 12 (12/8/2019) | Sportscasters Lost Cause vs 1st Avenue No Names |
| Week 12 (12/8/2019) | Risky's Rollin' Nerdy vs Madsen's The Leftovers |
| Week 13 (12/15/2019) | CJ's It's Miller Time vs 1st Avenue P V K |
| Week 13 (12/15/2019) | 1st Avenue No Names vs Risky's Rollin' Nerdy |
| Week 13 (12/15/2019) | Madsen's The Leftovers vs Sportscasters Lost Cause |
| Week 14 (12/22/2019) | Madsen's The Leftovers vs 1st Avenue No Names |
| Week 14 (12/22/2019) | 1st Avenue P V K vs Rosie's South Raptors |
| Week 14 (12/22/2019) | Risky's Rollin' Nerdy vs Sportscasters Lost Cause |
| Week of 12/29/2019 | No Leagues - Happy Holidays! |
| Week of 1/5/2020 | No Leagues - Happy New Year! |
| Week 15 (1/12/2020) | CJ's It's Miller Time vs 1st Avenue No Names |
| Week 15 (1/12/2020) | Rosie's South Raptors vs Sportscasters Lost Cause |
| Week 15 (1/12/2020) | 1st Avenue P V K vs Risky's Rollin' Nerdy |
| Week 16 (1/19/2020) | Sportscasters Lost Cause vs CJ's It's Miller Time |
| Week 16 (1/19/2020) | Madsen's The Leftovers vs 1st Avenue P V K |
| Week 16 (1/19/2020) | Risky's Rollin' Nerdy vs Rosie's South Raptors |
| Week 17 (1/26/2020) | CJ's It's Miller Time vs Madsen's The Leftovers |
| Week 17 (1/26/2020) | Rosie's South Raptors vs 1st Avenue No Names |
| Week 17 (1/26/2020) | 1st Avenue P V K vs Sportscasters Lost Cause |
| Week of 2/2/2020 | No Leagues - Super Bowl Sunday! |
| Week 18 (2/9/2020) | 1st Avenue No Names vs 1st Avenue P V K |
| Week 18 (2/9/2020) | Madsen's The Leftovers vs Rosie's South Raptors |
| Week 18 (2/9/2020) | Risky's Rollin' Nerdy vs CJ's It's Miller Time |
| Week 19 (2/16/2020) | CJ's It's Miller Time vs Rosie's South Raptors |
| Week 19 (2/16/2020) | 1st Avenue No Names vs Sportscasters Lost Cause |
| Week 19 (2/16/2020) | Madsen's The Leftovers vs Risky's Rollin' Nerdy |
| Week 20 (2/23/2020) | Sportscasters Lost Cause vs Madsen's The Leftovers |
| Week 20 (2/23/2020) | 1st Avenue P V K vs CJ's It's Miller Time |
| Week 20 (2/23/2020) | Risky's Rollin' Nerdy vs 1st Avenue No Names |
| Week 21 (3/1/2020) | 1st Avenue No Names vs Madsen's The Leftovers |
| Week 21 (3/1/2020) | Rosie's South Raptors vs 1st Avenue P V K |
| Week 21 (3/1/2020) | Sportscasters Lost Cause vs Risky's Rollin' Nerdy |