| Week 1 (9/16/2020) | WC's South WWCD vs Madsen's Not Today! @ Madsen's |
| Week 1 (9/16/2020) | Trackside Scratch This vs CJ's Misfits |
| Week 1 (9/16/2020) | WC's South Dive Bar Champions vs Risky's Cue Tips |
| Week 1 (9/16/2020) | Risky's D vs Risky's Rack N Roll |
| Week 2 (9/23/2020) | Risky's Rack N Roll vs Trackside Scratch This |
| Week 2 (9/23/2020) | Risky's Cue Tips vs WC's South WWCD |
| Week 2 (9/23/2020) | CJ's Misfits vs WC's South Dive Bar Champions |
| Week 2 (9/23/2020) | Madsen's Not Today! vs Risky's D |
| Week 3 (9/30/2020) | WC's South WWCD vs Risky's Rack N Roll |
| Week 3 (9/30/2020) | Trackside Scratch This vs Risky's Cue Tips |
| Week 3 (9/30/2020) | WC's South Dive Bar Champions vs Madsen's Not Today! @ Moonshiner's |
| Week 3 (9/30/2020) | Risky's D vs CJ's Misfits |
| Week 4 (10/7/2020) | Risky's Rack N Roll vs WC's South Dive Bar Champions |
| Week 4 (10/7/2020) | Risky's Cue Tips vs Risky's D |
| Week 4 (10/7/2020) | CJ's Misfits vs WC's South WWCD |
| Week 4 (10/7/2020) | Madsen's Not Today! vs Trackside Scratch This |
| Week 5 (10/14/2020) | WC's South WWCD vs WC's South Dive Bar Champions |
| Week 5 (10/14/2020) | Risky's Rack N Roll vs CJ's Misfits |
| Week 5 (10/14/2020) | Risky's D vs Trackside Scratch This |
| Week 5 (10/14/2020) | Madsen's Not Today! vs Risky's Cue Tips |
| Week 6 (10/21/2020) | Trackside Scratch This vs WC's South WWCD |
| Week 6 (10/21/2020) | WC's South Dive Bar Champions vs Risky's D |
| Week 6 (10/21/2020) | Risky's Cue Tips vs Risky's Rack N Roll |
| Week 6 (10/21/2020) | CJ's Misfits vs Madsen's Not Today! |
| Week 7 (10/28/2020) | WC's South WWCD vs Risky's D @ Rosie's South |
| Week 7 (10/28/2020) | WC's South Dive Bar Champions vs Trackside Scratch This |
| Week 7 (10/28/2020) | Risky's Cue Tips vs CJ's Misfits |
| Week 7 (10/28/2020) | Madsen's Not Today! vs Risky's Rack N Roll |
| Week 8 (11/4/2020) | Risky's Rack N Roll vs Risky's D |
| Week 8 (11/4/2020) | Risky's Cue Tips vs WC's South Dive Bar Champions |
| Week 8 (11/4/2020) | CJ's Misfits vs Trackside Scratch This |
| Week 8 (11/4/2020) | Madsen's Not Today! vs WC's South WWCD |
| Week 9 (11/11/2020) | WC's South WWCD vs Risky's Cue Tips |
| Week 9 (11/11/2020) | Trackside Scratch This vs Risky's Rack N Roll |
| Week 9 (11/11/2020) | WC's South Dive Bar Champions vs CJ's Misfits @ Rosie's South |
| Week 9 (11/11/2020) | Risky's D vs Madsen's Not Today! |
| Week 10 (11/18/2020) | Trackside Scratch This vs WC's South WWCD @ Madsen's |
| Week 10 (11/18/2020) | Risky's Cue Tips vs Risky's D |
| Week 10 (11/18/2020) | CJ's Misfits vs WC's South Dive Bar Champions @ Risky's |
| Week 10 (11/18/2020) | Madsen's Not Today! vs Risky's Rack N Roll @ CJ's |
| Week of 11/25/2020 | No Leagues - Happy Thanksgiving! |
| Week of 12/2/2020 | No Leagues - COVID DHMs |
| Week of 12/9/2020 | No Leagues - COVID DHMs |
| Week of 12/16/2020 | No Leagues - COVID DHMs |
| Week of 12/23/2020 | No Leagues - Merry Christmas! |
| Week of 12/30/2020 | No Leagues - Happy New Year! |
| Week 11 (1/6/2021) | WC's South WWCD vs Trackside Scratch This |
| Week 11 (1/6/2021) | Risky's Rack N Roll vs Risky's Cue Tips |
| Week 11 (1/6/2021) | Risky's D vs WC's South Dive Bar Champions |
| Week 11 (1/6/2021) | Madsen's Not Today! vs CJ's Misfits |
| Week 12 (1/13/2021) | Trackside Scratch This vs WC's South Dive Bar Champions |
| Week 12 (1/13/2021) | Risky's Rack N Roll vs Madsen's Not Today! |
| Week 12 (1/13/2021) | Risky's D vs WC's South WWCD |
| Week 12 (1/13/2021) | CJ's Misfits vs Risky's Cue Tips |
| Week 13 (1/20/2021) | WC's South WWCD vs Madsen's Not Today! |
| Week 13 (1/20/2021) | Trackside Scratch This vs CJ's Misfits |
| Week 13 (1/20/2021) | WC's South Dive Bar Champions vs Risky's Cue Tips @ Rosie's South |
| Week 13 (1/20/2021) | Risky's D vs Risky's Rack N Roll |
| Week 14 (1/27/2021) | Risky's Rack N Roll vs Trackside Scratch This |
| Week 14 (1/27/2021) | Risky's Cue Tips vs WC's South WWCD |
| Week 14 (1/27/2021) | CJ's Misfits vs WC's South Dive Bar Champions |
| Week 14 (1/27/2021) | Madsen's Not Today! vs Risky's D |
| Week 15 (2/3/2021) | WC's South WWCD vs Risky's Rack N Roll @ Rosie's South |
| Week 15 (2/3/2021) | Trackside Scratch This vs Risky's Cue Tips |
| Week 15 (2/3/2021) | WC's South Dive Bar Champions vs Madsen's Not Today! |
| Week 15 (2/3/2021) | Risky's D vs CJ's Misfits |
| Week 16 (2/10/2021) | Risky's Rack N Roll vs WC's South Dive Bar Champions |
| Week 16 (2/10/2021) | Risky's Cue Tips vs Risky's D |
| Week 16 (2/10/2021) | CJ's Misfits vs WC's South WWCD |
| Week 16 (2/10/2021) | Madsen's Not Today! vs Trackside Scratch This |
| Week 17 (2/17/2021) | WC's South WWCD vs WC's South Dive Bar Champions |
| Week 17 (2/17/2021) | Risky's Rack N Roll vs CJ's Misfits |
| Week 17 (2/17/2021) | Risky's D vs Trackside Scratch This |
| Week 17 (2/17/2021) | Madsen's Not Today! vs Risky's Cue Tips |
| Week 18 (2/24/2021) | Trackside Scratch This vs WC's South WWCD |
| Week 18 (2/24/2021) | WC's South Dive Bar Champions vs Risky's D |
| Week 18 (2/24/2021) | Risky's Cue Tips vs Risky's Rack N Roll |
| Week 18 (2/24/2021) | CJ's Misfits vs Madsen's Not Today! |
| Week 19 (3/3/2021) | WC's South WWCD vs Risky's D |
| Week 19 (3/3/2021) | WC's South Dive Bar Champions vs Trackside Scratch This @ Rosie's South |
| Week 19 (3/3/2021) | Risky's Cue Tips vs CJ's Misfits |
| Week 19 (3/3/2021) | Madsen's Not Today! vs Risky's Rack N Roll |