| Result | Tournament |
|---|---|
| Holden Bullock defeated Jason Woosley | 2023 High Roller 6 & Under 9-Ball |
| Braxton Westmoreland defeated Jason Woosley | 2023 High Roller 6 & Under 9-Ball |
| Jason Woosley defeated Adam Haines | 2016 Derby City Classic Bank Pool |
| Jason Woosley defeated Ahmad Raheem | 2016 Derby City Classic Bank Pool |
| Michael Wong defeated Jason Woosley | 2016 Derby City Classic Bank Pool |
| David Strawn Sr. defeated Jason Woosley | 2016 Derby City Classic Bank Pool |
| Jason Woosley defeated Steve Tetino | 2013 Derby City Classic One Pocket |
| Joe Gay defeated Jason Woosley | 2013 Derby City Classic One Pocket |
| Mike Brown defeated Jason Woosley | 2013 Derby City Classic One Pocket |
| Shaun Wilkie defeated Jason Woosley | 2012 Derby City Classic Bank Pool |