| Week 1 (4/11/2019) | Rosie's South Rosie's Castaways vs Madsen's Hot Lips Hooligan & the Pooligans |
| Week 1 (4/11/2019) | Risky's REX vs Playmaker's Blown Run Outs |
| Week 1 (4/11/2019) | Steve O's Team America vs Risky's Outlaws |
| Week 1 (4/11/2019) | Madsen's WooHoo vs WC's South Felt Up |
| Week 2 (4/18/2019) | Madsen's Hot Lips Hooligan & the Pooligans vs Steve O's Team America |
| Week 2 (4/18/2019) | Playmaker's Blown Run Outs vs Rosie's South Rosie's Castaways |
| Week 2 (4/18/2019) | Risky's Outlaws vs Madsen's WooHoo |
| Week 2 (4/18/2019) | WC's South Felt Up vs Risky's REX |
| Week of 4/25/2019 | No Leagues - Midwest Pool Tournament |
| Week 3 (5/2/2019) | Rosie's South Rosie's Castaways vs Risky's Outlaws |
| Week 3 (5/2/2019) | Risky's REX vs Madsen's Hot Lips Hooligan & the Pooligans |
| Week 3 (5/2/2019) | Steve O's Team America vs WC's South Felt Up |
| Week 3 (5/2/2019) | Madsen's WooHoo vs Playmaker's Blown Run Outs |
| Week 4 (5/9/2019) | Madsen's Hot Lips Hooligan & the Pooligans vs Madsen's WooHoo |
| Week 4 (5/9/2019) | Playmaker's Blown Run Outs vs Steve O's Team America |
| Week 4 (5/9/2019) | Risky's Outlaws vs Risky's REX |
| Week 4 (5/9/2019) | WC's South Felt Up vs Rosie's South Rosie's Castaways |
| Week 5 (5/16/2019) | Rosie's South Rosie's Castaways vs Risky's REX |
| Week 5 (5/16/2019) | Madsen's Hot Lips Hooligan & the Pooligans vs Playmaker's Blown Run Outs |
| Week 5 (5/16/2019) | Steve O's Team America vs Madsen's WooHoo |
| Week 5 (5/16/2019) | Risky's Outlaws vs WC's South Felt Up |
| Week 6 (5/23/2019) | Risky's REX vs Steve O's Team America |
| Week 6 (5/23/2019) | Playmaker's Blown Run Outs vs Risky's Outlaws |
| Week 6 (5/23/2019) | WC's South Felt Up vs Madsen's Hot Lips Hooligan & the Pooligans |
| Week 6 (5/23/2019) | Madsen's WooHoo vs Rosie's South Rosie's Castaways |
| Week 7 (5/30/2019) | Rosie's South Rosie's Castaways vs Steve O's Team America |
| Week 7 (5/30/2019) | Madsen's Hot Lips Hooligan & the Pooligans vs Risky's Outlaws |
| Week 7 (5/30/2019) | Risky's REX vs Madsen's WooHoo |
| Week 7 (5/30/2019) | Playmaker's Blown Run Outs vs WC's South Felt Up |
| Week 8 (6/6/2019) | Madsen's Hot Lips Hooligan & the Pooligans vs Rosie's South Rosie's Castaways |
| Week 8 (6/6/2019) | Playmaker's Blown Run Outs vs Risky's REX |
| Week 8 (6/6/2019) | Risky's Outlaws vs Steve O's Team America |
| Week 8 (6/6/2019) | WC's South Felt Up vs Madsen's WooHoo |
| Week 9 (6/13/2019) | Rosie's South Rosie's Castaways vs Playmaker's Blown Run Outs |
| Week 9 (6/13/2019) | Risky's REX vs WC's South Felt Up |
| Week 9 (6/13/2019) | Steve O's Team America vs Madsen's Hot Lips Hooligan & the Pooligans |
| Week 9 (6/13/2019) | Madsen's WooHoo vs Risky's Outlaws |
| Week 10 (6/20/2019) | Madsen's Hot Lips Hooligan & the Pooligans vs Risky's REX |
| Week 10 (6/20/2019) | Playmaker's Blown Run Outs vs Madsen's WooHoo |
| Week 10 (6/20/2019) | Risky's Outlaws vs Rosie's South Rosie's Castaways |
| Week 10 (6/20/2019) | WC's South Felt Up vs Steve O's Team America |
| Week 11 (6/27/2019) | Rosie's South Rosie's Castaways vs WC's South Felt Up |
| Week 11 (6/27/2019) | Risky's REX vs Risky's Outlaws |
| Week 11 (6/27/2019) | Steve O's Team America vs Playmaker's Blown Run Outs |
| Week 11 (6/27/2019) | Madsen's WooHoo vs Madsen's Hot Lips Hooligan & the Pooligans |