| Dennis Orcollo | Sky Woodward | 4 - Wins | 2 - Wins |
|---|
| Match | Tournament |
|---|---|
| Sky Woodward defeated Dennis Orcollo | 2018 Derby City Classic Bank Pool |
| Sky Woodward defeated Dennis Orcollo | 2019 Derby City Classic 9-Ball |
| Dennis Orcollo defeated Sky Woodward | 2014 Derby City Classic One Pocket |
| Dennis Orcollo defeated Sky Woodward | 2015 Derby City Classic 9-Ball |
| Dennis Orcollo defeated Sky Woodward | 2015 U.S.Open 9-Ball |
| Dennis Orcollo defeated Sky Woodward | 2017 Derby City Classic One Pocket |