| Week 1 (9/9/2019) | Sportscasters 50 Killers vs Big Sal's Regulators |
| Week 1 (9/9/2019) | Madsen's Grim Reapers vs Steve O's Crazy 8s |
| Week 1 (9/9/2019) | WC's South Rude Boyz vs Rosie's South Rail Riders |
| Week 2 (9/16/2019) | Big Sal's Regulators vs WC's South Rude Boyz |
| Week 2 (9/16/2019) | Rosie's South Rail Riders vs Madsen's Grim Reapers |
| Week 2 (9/16/2019) | Steve O's Crazy 8s vs Sportscasters 50 Killers |
| Week 3 (9/23/2019) | Madsen's Grim Reapers vs Big Sal's Regulators |
| Week 3 (9/23/2019) | Steve O's Crazy 8s vs Rosie's South Rail Riders |
| Week 3 (9/23/2019) | WC's South Rude Boyz vs Sportscasters 50 Killers |
| Week 4 (9/30/2019) | Big Sal's Regulators vs Steve O's Crazy 8s |
| Week 4 (9/30/2019) | Sportscasters 50 Killers vs Rosie's South Rail Riders |
| Week 4 (9/30/2019) | WC's South Rude Boyz vs Madsen's Grim Reapers |
| Week 5 (10/7/2019) | Rosie's South Rail Riders vs Big Sal's Regulators |
| Week 5 (10/7/2019) | Madsen's Grim Reapers vs Sportscasters 50 Killers |
| Week 5 (10/7/2019) | Steve O's Crazy 8s vs WC's South Rude Boyz |
| Week 6 (10/14/2019) | Big Sal's Regulators vs Sportscasters 50 Killers |
| Week 6 (10/14/2019) | Rosie's South Rail Riders vs WC's South Rude Boyz |
| Week 6 (10/14/2019) | Steve O's Crazy 8s vs Madsen's Grim Reapers |
| Week 7 (10/21/2019) | Sportscasters 50 Killers vs Steve O's Crazy 8s |
| Week 7 (10/21/2019) | Madsen's Grim Reapers vs Rosie's South Rail Riders |
| Week 7 (10/21/2019) | WC's South Rude Boyz vs Big Sal's Regulators |
| Week 8 (10/28/2019) | Big Sal's Regulators vs Madsen's Grim Reapers |
| Week 8 (10/28/2019) | Sportscasters 50 Killers vs WC's South Rude Boyz |
| Week 8 (10/28/2019) | Rosie's South Rail Riders vs Steve O's Crazy 8s |
| Week 9 (11/4/2019) | Rosie's South Rail Riders vs Sportscasters 50 Killers |
| Week 9 (11/4/2019) | Madsen's Grim Reapers vs WC's South Rude Boyz |
| Week 9 (11/4/2019) | Steve O's Crazy 8s vs Big Sal's Regulators |
| Week 10 (11/11/2019) | Big Sal's Regulators vs Rosie's South Rail Riders |
| Week 10 (11/11/2019) | Sportscasters 50 Killers vs Madsen's Grim Reapers |
| Week 10 (11/11/2019) | WC's South Rude Boyz vs Steve O's Crazy 8s |
| Week 11 (11/18/2019) | Sportscasters 50 Killers vs Big Sal's Regulators |
| Week 11 (11/18/2019) | Madsen's Grim Reapers vs Steve O's Crazy 8s |
| Week 11 (11/18/2019) | WC's South Rude Boyz vs Rosie's South Rail Riders |
| Week of 11/25/2019 | No Leagues - Happy Thanksgiving! |
| Week 12 (12/2/2019) | Big Sal's Regulators vs WC's South Rude Boyz |
| Week 12 (12/2/2019) | Rosie's South Rail Riders vs Madsen's Grim Reapers |
| Week 12 (12/2/2019) | Steve O's Crazy 8s vs Sportscasters 50 Killers |
| Week 13 (12/9/2019) | Madsen's Grim Reapers vs Big Sal's Regulators |
| Week 13 (12/9/2019) | Steve O's Crazy 8s vs Rosie's South Rail Riders |
| Week 13 (12/9/2019) | WC's South Rude Boyz vs Sportscasters 50 Killers |
| Week 14 (12/16/2019) | Big Sal's Regulators vs Steve O's Crazy 8s |
| Week 14 (12/16/2019) | Sportscasters 50 Killers vs Rosie's South Rail Riders |
| Week 14 (12/16/2019) | WC's South Rude Boyz vs Madsen's Grim Reapers |
| Week of 12/23/2019 | No Leagues - Happy Holidays! |
| Week of 12/30/2019 | No Leagues - Happy New Year! |
| Week 15 (1/6/2020) | Rosie's South Rail Riders vs Big Sal's Regulators |
| Week 15 (1/6/2020) | Madsen's Grim Reapers vs Sportscasters 50 Killers |
| Week 15 (1/6/2020) | Steve O's Crazy 8s vs WC's South Rude Boyz |
| Week 16 (1/13/2020) | Madsen's Grim Reapers vs Rosie's South Rail Riders @ Steve O's |
| Week 16 (1/13/2020) | Steve O's Crazy 8s vs Big Sal's Regulators @ WC's South |
| Week 16 (1/13/2020) | WC's South Rude Boyz vs Sportscasters 50 Killers @ Madsen's |
| Week 17 (1/20/2020) | Big Sal's Regulators vs Sportscasters 50 Killers |
| Week 17 (1/20/2020) | Rosie's South Rail Riders vs WC's South Rude Boyz |
| Week 17 (1/20/2020) | Steve O's Crazy 8s vs Madsen's Grim Reapers |
| Week 18 (1/27/2020) | Sportscasters 50 Killers vs Steve O's Crazy 8s |
| Week 18 (1/27/2020) | Madsen's Grim Reapers vs Rosie's South Rail Riders |
| Week 18 (1/27/2020) | WC's South Rude Boyz vs Big Sal's Regulators |
| Week 19 (2/3/2020) | Big Sal's Regulators vs Madsen's Grim Reapers |
| Week 19 (2/3/2020) | Sportscasters 50 Killers vs WC's South Rude Boyz |
| Week 19 (2/3/2020) | Rosie's South Rail Riders vs Steve O's Crazy 8s |
| Week 20 (2/10/2020) | Rosie's South Rail Riders vs Sportscasters 50 Killers |
| Week 20 (2/10/2020) | Madsen's Grim Reapers vs WC's South Rude Boyz |
| Week 20 (2/10/2020) | Steve O's Crazy 8s vs Big Sal's Regulators |
| Week 21 (2/17/2020) | Big Sal's Regulators vs Rosie's South Rail Riders |
| Week 21 (2/17/2020) | Sportscasters 50 Killers vs Madsen's Grim Reapers |
| Week 21 (2/17/2020) | WC's South Rude Boyz vs Steve O's Crazy 8s |
| Week 22 (2/24/2020) | Big Sal's Regulators vs Steve O's Crazy 8s @ Rosie's South |
| Week 22 (2/24/2020) | Sportscasters 50 Killers vs WC's South Rude Boyz @ Madsen's |
| Week 22 (2/24/2020) | Rosie's South Rail Riders vs Madsen's Grim Reapers @ Sportscasters |