| Week 1 (9/12/2019) | Madsen's Throwbacks vs Madsen's Mass Chaos |
| Week 1 (9/12/2019) | Rosie's South Castaways vs Big Sal's Old Duffers |
| Week 1 (9/12/2019) | Kelli's Pub Here For Beer vs Steve O's The Chalking Dead |
| Week 1 (9/12/2019) | Madsen's I Don't Care vs Cappy's Odds & Ends |
| Week 2 (9/19/2019) | Madsen's Mass Chaos vs Kelli's Pub Here For Beer |
| Week 2 (9/19/2019) | Big Sal's Old Duffers vs Madsen's Throwbacks @ Braska Bar |
| Week 2 (9/19/2019) | Steve O's The Chalking Dead vs Madsen's I Don't Care |
| Week 2 (9/19/2019) | Cappy's Odds & Ends vs Rosie's South Castaways |
| Week 3 (9/26/2019) | Madsen's Throwbacks vs Steve O's The Chalking Dead |
| Week 3 (9/26/2019) | Rosie's South Castaways vs Madsen's Mass Chaos |
| Week 3 (9/26/2019) | Kelli's Pub Here For Beer vs Cappy's Odds & Ends |
| Week 3 (9/26/2019) | Madsen's I Don't Care vs Big Sal's Old Duffers |
| Week 4 (10/3/2019) | Madsen's Mass Chaos vs Madsen's I Don't Care |
| Week 4 (10/3/2019) | Big Sal's Old Duffers vs Kelli's Pub Here For Beer @ Braska Bar |
| Week 4 (10/3/2019) | Steve O's The Chalking Dead vs Rosie's South Castaways |
| Week 4 (10/3/2019) | Cappy's Odds & Ends vs Madsen's Throwbacks |
| Week 5 (10/10/2019) | Madsen's Throwbacks vs Rosie's South Castaways |
| Week 5 (10/10/2019) | Madsen's Mass Chaos vs Big Sal's Old Duffers |
| Week 5 (10/10/2019) | Kelli's Pub Here For Beer vs Madsen's I Don't Care |
| Week 5 (10/10/2019) | Steve O's The Chalking Dead vs Cappy's Odds & Ends |
| Week 6 (10/17/2019) | Rosie's South Castaways vs Kelli's Pub Here For Beer |
| Week 6 (10/17/2019) | Big Sal's Old Duffers vs Steve O's The Chalking Dead @ Braska Bar |
| Week 6 (10/17/2019) | Madsen's I Don't Care vs Madsen's Throwbacks |
| Week 6 (10/17/2019) | Cappy's Odds & Ends vs Madsen's Mass Chaos |
| Week 7 (10/24/2019) | Madsen's Throwbacks vs Kelli's Pub Here For Beer |
| Week 7 (10/24/2019) | Madsen's Mass Chaos vs Steve O's The Chalking Dead |
| Week 7 (10/24/2019) | Rosie's South Castaways vs Madsen's I Don't Care @ Storm Cellar |
| Week 7 (10/24/2019) | Big Sal's Old Duffers vs Cappy's Odds & Ends @ Braska Bar |
| Week 8 (10/31/2019) | Madsen's Mass Chaos vs Madsen's Throwbacks |
| Week 8 (10/31/2019) | Big Sal's Old Duffers vs Rosie's South Castaways @ Braska Bar |
| Week 8 (10/31/2019) | Steve O's The Chalking Dead vs Kelli's Pub Here For Beer |
| Week 8 (10/31/2019) | Cappy's Odds & Ends vs Madsen's I Don't Care |
| Week 9 (11/7/2019) | Madsen's Throwbacks vs Big Sal's Old Duffers |
| Week 9 (11/7/2019) | Rosie's South Castaways vs Cappy's Odds & Ends |
| Week 9 (11/7/2019) | Kelli's Pub Here For Beer vs Madsen's Mass Chaos @ Sportscasters |
| Week 9 (11/7/2019) | Madsen's I Don't Care vs Steve O's The Chalking Dead |
| Week 10 (11/14/2019) | Madsen's Mass Chaos vs Rosie's South Castaways |
| Week 10 (11/14/2019) | Big Sal's Old Duffers vs Madsen's I Don't Care @ Braska Bar |
| Week 10 (11/14/2019) | Steve O's The Chalking Dead vs Madsen's Throwbacks |
| Week 10 (11/14/2019) | Cappy's Odds & Ends vs Kelli's Pub Here For Beer |
| Week 11 (11/21/2019) | Madsen's Throwbacks vs Steve O's The Chalking Dead @ Braska Bar |
| Week 11 (11/21/2019) | Kelli's Pub Here For Beer vs Madsen's Mass Chaos @ Steve O's |
| Week 11 (11/21/2019) | Madsen's I Don't Care vs Big Sal's Old Duffers @ Cappy's |
| Week 11 (11/21/2019) | Cappy's Odds & Ends vs Rosie's South Castaways @ Madsen's |
| Week of 11/28/2019 | No Leagues - Happy Thanksgiving! |
| Week 12 (12/5/2019) | Madsen's Throwbacks vs Cappy's Odds & Ends |
| Week 12 (12/5/2019) | Rosie's South Castaways vs Steve O's The Chalking Dead |
| Week 12 (12/5/2019) | Kelli's Pub Here For Beer vs Big Sal's Old Duffers @ Sportscasters |
| Week 12 (12/5/2019) | Madsen's I Don't Care vs Madsen's Mass Chaos |
| Week 13 (12/12/2019) | Rosie's South Castaways vs Madsen's Throwbacks |
| Week 13 (12/12/2019) | Big Sal's Old Duffers vs Madsen's Mass Chaos @ Braska Bar |
| Week 13 (12/12/2019) | Madsen's I Don't Care vs Kelli's Pub Here For Beer |
| Week 13 (12/12/2019) | Cappy's Odds & Ends vs Steve O's The Chalking Dead |
| Week 14 (12/19/2019) | Madsen's Throwbacks vs Madsen's I Don't Care |
| Week 14 (12/19/2019) | Madsen's Mass Chaos vs Cappy's Odds & Ends |
| Week 14 (12/19/2019) | Kelli's Pub Here For Beer vs Rosie's South Castaways @ Brewsky's South |
| Week 14 (12/19/2019) | Steve O's The Chalking Dead vs Big Sal's Old Duffers |
| Week of 12/26/2019 | No Leagues - Happy Holidays! |
| Week of 1/2/2020 | No Leagues - Happy New Year! |
| Week 15 (1/9/2020) | Kelli's Pub Here For Beer vs Madsen's Throwbacks @ Brewsky's South |
| Week 15 (1/9/2020) | Steve O's The Chalking Dead vs Madsen's Mass Chaos |
| Week 15 (1/9/2020) | Madsen's I Don't Care vs Rosie's South Castaways |
| Week 15 (1/9/2020) | Cappy's Odds & Ends vs Big Sal's Old Duffers |
| Week 16 (1/16/2020) | Madsen's Throwbacks vs Madsen's Mass Chaos |
| Week 16 (1/16/2020) | Rosie's South Castaways vs Big Sal's Old Duffers |
| Week 16 (1/16/2020) | Kelli's Pub Here For Beer vs Steve O's The Chalking Dead @ Sportscasters |
| Week 16 (1/16/2020) | Madsen's I Don't Care vs Cappy's Odds & Ends |
| Week 17 (1/23/2020) | Madsen's Mass Chaos vs Kelli's Pub Here For Beer |
| Week 17 (1/23/2020) | Big Sal's Old Duffers vs Madsen's Throwbacks @ Braska Bar |
| Week 17 (1/23/2020) | Steve O's The Chalking Dead vs Madsen's I Don't Care |
| Week 17 (1/23/2020) | Cappy's Odds & Ends vs Rosie's South Castaways |
| Week 18 (1/30/2020) | Madsen's Throwbacks vs Steve O's The Chalking Dead |
| Week 18 (1/30/2020) | Rosie's South Castaways vs Madsen's Mass Chaos |
| Week 18 (1/30/2020) | Kelli's Pub Here For Beer vs Cappy's Odds & Ends @ Sportscasters |
| Week 18 (1/30/2020) | Madsen's I Don't Care vs Big Sal's Old Duffers |
| Week 19 (2/6/2020) | Madsen's Mass Chaos vs Madsen's I Don't Care |
| Week 19 (2/6/2020) | Big Sal's Old Duffers vs Kelli's Pub Here For Beer |
| Week 19 (2/6/2020) | Steve O's The Chalking Dead vs Rosie's South Castaways |
| Week 19 (2/6/2020) | Cappy's Odds & Ends vs Madsen's Throwbacks |
| Week 20 (2/13/2020) | Madsen's Throwbacks vs Rosie's South Castaways |
| Week 20 (2/13/2020) | Madsen's Mass Chaos vs Big Sal's Old Duffers |
| Week 20 (2/13/2020) | Kelli's Pub Here For Beer vs Madsen's I Don't Care @ Brewsky's South |
| Week 20 (2/13/2020) | Steve O's The Chalking Dead vs Cappy's Odds & Ends |
| Week 21 (2/20/2020) | Rosie's South Castaways vs Kelli's Pub Here For Beer |
| Week 21 (2/20/2020) | Big Sal's Old Duffers vs Steve O's The Chalking Dead |
| Week 21 (2/20/2020) | Madsen's I Don't Care vs Madsen's Throwbacks |
| Week 21 (2/20/2020) | Cappy's Odds & Ends vs Madsen's Mass Chaos |
| Week 22 (2/27/2020) | Madsen's Throwbacks vs Kelli's Pub Here For Beer |
| Week 22 (2/27/2020) | Madsen's Mass Chaos vs Steve O's The Chalking Dead |
| Week 22 (2/27/2020) | Rosie's South Castaways vs Madsen's I Don't Care |
| Week 22 (2/27/2020) | Big Sal's Old Duffers vs Cappy's Odds & Ends |