| Week 1 (7/17/2019) | Steve O's Neat With A Twist vs Madsen's Pretty Awesome |
| Week 1 (7/17/2019) | Madsen's Fireball Express vs Steve O's On The Rocks |
| Week 1 (7/17/2019) | Rosie's South We're Solids Right? vs Risky's Red Owl Coonrod |
| Week 2 (7/24/2019) | Steve O's On The Rocks vs Rosie's South We're Solids Right? |
| Week 2 (7/24/2019) | Risky's Red Owl Coonrod vs Steve O's Neat With A Twist |
| Week 2 (7/24/2019) | Madsen's Pretty Awesome vs Madsen's Fireball Express |
| Week 3 (7/31/2019) | Steve O's Neat With A Twist vs Steve O's On The Rocks |
| Week 3 (7/31/2019) | Rosie's South We're Solids Right? vs Madsen's Fireball Express |
| Week 3 (7/31/2019) | Madsen's Pretty Awesome vs Risky's Red Owl Coonrod |
| Week 4 (8/7/2019) | Steve O's On The Rocks vs Madsen's Pretty Awesome |
| Week 4 (8/7/2019) | Madsen's Fireball Express vs Risky's Red Owl Coonrod |
| Week 4 (8/7/2019) | Rosie's South We're Solids Right? vs Steve O's Neat With A Twist |
| Week 5 (8/14/2019) | Steve O's Neat With A Twist vs Madsen's Fireball Express |
| Week 5 (8/14/2019) | Risky's Red Owl Coonrod vs Steve O's On The Rocks |
| Week 5 (8/14/2019) | Madsen's Pretty Awesome vs Rosie's South We're Solids Right? |
| Week 6 (8/21/2019) | Risky's Red Owl Coonrod vs Steve O's Neat With A Twist @ Madsen's |
| Week 6 (8/21/2019) | Madsen's Fireball Express vs Steve O's On The Rocks @ Risky's |
| Week 6 (8/21/2019) | Madsen's Pretty Awesome vs Rosie's South We're Solids Right? @ Steve O's |