| Result | Tournament |
|---|---|
| Tyler Perry defeated Jim Winter | 2019 28th Annual 4 Bears Classic |
| Jim Winter defeated Oj Grey Bear | 2019 28th Annual 4 Bears Classic |
| Jim Winter defeated Tim Cariveau | 2019 28th Annual 4 Bears Classic |
| Jim Winter defeated Scott Nelson | 2019 28th Annual 4 Bears Classic |
| Chris Larocque defeated Jim Winter | 2019 28th Annual 4 Bears Classic |
| Alex Bloms defeated Jim Winter | 2019 28th Annual 4 Bears Classic 8-Ball |
| Neal Burr defeated Jim Winter | 2019 28th Annual 4 Bears Classic 8-Ball |