| Week 1 (9/10/2019) | Time Clock S.O.B.'s vs Philly's Sticks & Stones @ Philly's |
| Week 1 (9/10/2019) | Harold's Bar Moritz vs Kozee Lounge OBSP+1 |
| Week 1 (9/10/2019) | Musette Bar Smurfettes vs Club 5216 Menichetti |
| Week 1 (9/10/2019) | Starsky's Dale vs Musette Bar Woods |
| Week 2 (9/17/2019) | Club 5216 Menichetti vs Starsky's Dale |
| Week 2 (9/17/2019) | Harold's Bar Moritz vs Shooters 8 Ball Ninja's |
| Week 2 (9/17/2019) | Musette Bar Smurfettes vs Time Clock S.O.B.'s |
| Week 2 (9/17/2019) | Kozee Lounge OBSP+1 vs Philly's Sticks & Stones |
| Week 3 (9/24/2019) | Club 5216 Menichetti vs Harold's Bar Moritz |
| Week 3 (9/24/2019) | Philly's Sticks & Stones vs Musette Bar Woods |
| Week 3 (9/24/2019) | Musette Bar Smurfettes vs Shooters 8 Ball Ninja's |
| Week 3 (9/24/2019) | Kozee Lounge OBSP+1 vs Starsky's Dale |
| Week 4 (10/1/2019) | Philly's Sticks & Stones vs Shooters 8 Ball Ninja's |
| Week 4 (10/1/2019) | Musette Bar Woods vs Harold's Bar Moritz |
| Week 4 (10/1/2019) | Kozee Lounge OBSP+1 vs Musette Bar Smurfettes |
| Week 4 (10/1/2019) | Starsky's Dale vs Time Clock S.O.B.'s @ 13th St Brickhouse |
| Week 5 (10/8/2019) | Club 5216 Menichetti vs Time Clock S.O.B.'s @ 13th St Brickhouse |
| Week 5 (10/8/2019) | Harold's Bar Moritz vs Philly's Sticks & Stones |
| Week 5 (10/8/2019) | Musette Bar Woods vs Musette Bar Smurfettes |
| Week 5 (10/8/2019) | Shooters 8 Ball Ninja's vs Kozee Lounge OBSP+1 |
| Week 6 (10/15/2019) | Harold's Bar Moritz vs Time Clock S.O.B.'s |
| Week 6 (10/15/2019) | Musette Bar Woods vs Kozee Lounge OBSP+1 |
| Week 6 (10/15/2019) | Shooters 8 Ball Ninja's vs Club 5216 Menichetti |
| Week 6 (10/15/2019) | Starsky's Dale vs Musette Bar Smurfettes |
| Week 7 (10/22/2019) | Club 5216 Menichetti vs Philly's Sticks & Stones |
| Week 7 (10/22/2019) | Harold's Bar Moritz vs Starsky's Dale |
| Week 7 (10/22/2019) | Musette Bar Woods vs Shooters 8 Ball Ninja's |
| Week 7 (10/22/2019) | Kozee Lounge OBSP+1 vs Time Clock S.O.B.'s |
| Week 8 (10/29/2019) | Time Clock S.O.B.'s vs Musette Bar Woods |
| Week 8 (10/29/2019) | Musette Bar Smurfettes vs Philly's Sticks & Stones |
| Week 8 (10/29/2019) | Kozee Lounge OBSP+1 vs Club 5216 Menichetti |
| Week 8 (10/29/2019) | Starsky's Dale vs Shooters 8 Ball Ninja's |
| Week 9 (11/5/2019) | Club 5216 Menichetti vs Musette Bar Woods |
| Week 9 (11/5/2019) | Philly's Sticks & Stones vs Starsky's Dale |
| Week 9 (11/5/2019) | Musette Bar Smurfettes vs Harold's Bar Moritz |
| Week 9 (11/5/2019) | Shooters 8 Ball Ninja's vs Time Clock S.O.B.'s |
| Week 10 (11/12/2019) | Time Clock S.O.B.'s vs Philly's Sticks & Stones |
| Week 10 (11/12/2019) | Club 5216 Menichetti vs Musette Bar Smurfettes |
| Week 10 (11/12/2019) | Musette Bar Woods vs Starsky's Dale |
| Week 10 (11/12/2019) | Kozee Lounge OBSP+1 vs Harold's Bar Moritz |
| Week 11 (11/19/2019) | Time Clock S.O.B.'s vs Musette Bar Smurfettes @ 13th St Brickhouse |
| Week 11 (11/19/2019) | Philly's Sticks & Stones vs Kozee Lounge OBSP+1 |
| Week 11 (11/19/2019) | Shooters 8 Ball Ninja's vs Harold's Bar Moritz |
| Week 11 (11/19/2019) | Starsky's Dale vs Club 5216 Menichetti |
| Week 12 (11/26/2019) | Harold's Bar Moritz vs Club 5216 Menichetti |
| Week 12 (11/26/2019) | Musette Bar Woods vs Philly's Sticks & Stones |
| Week 12 (11/26/2019) | Shooters 8 Ball Ninja's vs Musette Bar Smurfettes |
| Week 12 (11/26/2019) | Starsky's Dale vs Kozee Lounge OBSP+1 |
| Week 13 (12/3/2019) | Time Clock S.O.B.'s vs Starsky's Dale @ Starsky's |
| Week 13 (12/3/2019) | Harold's Bar Moritz vs Musette Bar Woods |
| Week 13 (12/3/2019) | Musette Bar Smurfettes vs Kozee Lounge OBSP+1 |
| Week 13 (12/3/2019) | Shooters 8 Ball Ninja's vs Philly's Sticks & Stones |
| Week 14 (12/10/2019) | Time Clock S.O.B.'s vs Club 5216 Menichetti @ Club 5216 |
| Week 14 (12/10/2019) | Philly's Sticks & Stones vs Harold's Bar Moritz |
| Week 14 (12/10/2019) | Musette Bar Smurfettes vs Musette Bar Woods |
| Week 14 (12/10/2019) | Kozee Lounge OBSP+1 vs Shooters 8 Ball Ninja's |
| Week 15 (12/17/2019) | Time Clock S.O.B.'s vs Harold's Bar Moritz |
| Week 15 (12/17/2019) | Club 5216 Menichetti vs Shooters 8 Ball Ninja's |
| Week 15 (12/17/2019) | Musette Bar Smurfettes vs Starsky's Dale |
| Week 15 (12/17/2019) | Kozee Lounge OBSP+1 vs Musette Bar Woods |
| Week of 12/24/2019 | No Leagues - Happy Holidays |
| Week of 12/31/2019 | No Leagues - Happy Holidays |
| Week 16 (1/7/2020) | Time Clock S.O.B.'s vs Kozee Lounge OBSP+1 |
| Week 16 (1/7/2020) | Philly's Sticks & Stones vs Club 5216 Menichetti |
| Week 16 (1/7/2020) | Shooters 8 Ball Ninja's vs Musette Bar Woods |
| Week 16 (1/7/2020) | Starsky's Dale vs Harold's Bar Moritz |
| Week 17 (1/14/2020) | Club 5216 Menichetti vs Kozee Lounge OBSP+1 |
| Week 17 (1/14/2020) | Philly's Sticks & Stones vs Musette Bar Smurfettes |
| Week 17 (1/14/2020) | Musette Bar Woods vs Time Clock S.O.B.'s |
| Week 17 (1/14/2020) | Shooters 8 Ball Ninja's vs Starsky's Dale |
| Week 18 (1/21/2020) | Time Clock S.O.B.'s vs Shooters 8 Ball Ninja's |
| Week 18 (1/21/2020) | Harold's Bar Moritz vs Musette Bar Smurfettes |
| Week 18 (1/21/2020) | Musette Bar Woods vs Club 5216 Menichetti |
| Week 18 (1/21/2020) | Starsky's Dale vs Philly's Sticks & Stones |