| # | Tournament | Winning Team | Winner Score | Losing Team | Loser Score |
| 1 | D Dual Qualifier | Bad Boy Softball | 11 | WinCity/Anthony's Restaurant & Pub | 10 |
| 2 | D Dual Qualifier | WinCity/Anthony's Restaur | 14 | GOODWOOD | 4 |
| 3 | D Dual Qualifier | Haymaker Softball | 15 | WinCity/Anthony's Restaurant & Pub | 5 |
| 4 | D Qualifier | WinCity/Anthony's Restaur | 12 | Skooters | 9 |
| 5 | D Qualifier | Hafenrichter Farms | 8 | WinCity/Anthony's Restaurant & Pub | 6 |
| 6* | D Qualifier | WinCity/Anthony's Restaur | 13 | Coldwell Banker Honig-Bel | 0 |
| 7 | D Qualifier | Skooters | 14 | WinCity/Anthony's Restaurant & Pub | 4 |
| 8* | Windy City Major | Investment Solution Servi | 22 | WinCity/Anthony's Restaurant & Pub | 20 |
| 9* | Windy City Major | Newbreed/GTS/Beus Excavat | 31 | WinCity/Anthony's Restaurant & Pub | 1 |
| 10 | D Qualifier | WinCity/Anthony's Restaur | 15 | Bad Boy Softball | 10 |
| 11* | D Qualifier | Wasted Talent | 7 | WinCity/Anthony's Restaurant & Pub | 6 |
| 12 | D Qualifier | WinCity/Anthony's Restaur | 21 | BLACKOUT | 20 |
| 13 | D Qualifier | Hafenrichter Farms | 17 | WinCity/Anthony's Restaurant & Pub | 5 |
| 14 | D Qualifier | LVP Nation | 13 | WinCity/Anthony's Restaurant & Pub | 11 |
| 15* | D Qualifier | WinCity/Anthony's Restaur | 13 | Coldwell Banker Honig-Bel | 12 |
| 16 | D Qualifier | WinCity/Anthony's Restaur | 13 | Hafenrichter Farms | 12 |
| 17 | D Qualifier | Showstoppas | 10 | WinCity/Anthony's Restaurant & Pub | 9 |
| 18 | Last Chance Qualifier D/E | Landsharks | 15 | WinCity/Anthony's Restaurant & Pub | 5 |
| 19 | Last Chance Qualifier D/E | WinCity/Anthony's Restaur | 16 | Caciques | 15 |
| 20* | Last Chance Qualifier D/E | WinCity/Anthony's Restaur | 14 | The Orphans | 9 |
| 21* | Last Chance Qualifier D/E | WinCity/Anthony's Restaur | 28 | Comeback Kidz | 7 |
| 22* | Last Chance Qualifier D/E | Xtreme Softball | 18 | WinCity/Anthony's Restaurant & Pub | 14 |
| 23 | Illinois OPEN Conference STATE | Hafenrichter Farms | 20 | WinCity/Anthony's Restaurant & Pub | 17 |
| 24* | Illinois OPEN Conference STATE | Past Time Softball | 12 | WinCity/Anthony's Restaurant & Pub | 2 |
| 25 | D State | Bad Boy Softball | 11 | WinCity/Anthony's Restaurant & Pub | 6 |
| 26 | D State | Hafenrichter Farms | 14 | WinCity/Anthony's Restaurant & Pub | 6 |
| 27* | Great Lakes D National | WinCity/Anthony's Restaur | 10 | Widow Makers | 8 |
| 28 | Great Lakes D National | Haymaker Softball | 20 | WinCity/Anthony's Restaurant & Pub | 5 |
| 29 | Great Lakes D National | WinCity/Anthony's Restaur | 15 | TEAM CHITOWN | 2 |
| 30 | Great Lakes D National | Dad Bods | 15 | WinCity/Anthony's Restaurant & Pub | 12 |
| 31 | USSSA Men's D World Tournament | WinCity/Anthony's Restaur | 19 | New Holland Legion | 13 |
| 32 | USSSA Men's D World Tournament | WinCity/Anthony's Restaur | 12 | UWR | 4 |
| 33 | USSSA Men's D World Tournament | WinCity/Anthony's Restaur | 12 | QT/LIE/Kekambas | 11 |
| 34 | USSSA Men's D World Tournament | Conference | 21 | WinCity/Anthony's Restaurant & Pub | 10 |
| 35 | USSSA Men's D World Tournament | CT Hitmen/2312Sportswear/ | 2 | WinCity/Anthony's Restaurant & Pub | 0 |
| 36 | USSSA Men's D World Tournament | CT Hitmen/2312Sportswear/ | 14 | WinCity/Anthony's Restaurant & Pub | 7 |
* Indicates games played against teams of different class. Updated every night. The first day results are entered all games will appear in tan. |