| Sky Woodward | Jayson Shaw | 2 - Wins | 3 - Wins |
|---|
| Match | Tournament |
|---|---|
| Sky Woodward defeated Jayson Shaw | 2013 Derby City Classic One Pocket |
| Sky Woodward defeated Jayson Shaw | 2017 Derby City Classic 9-Ball |
| Jayson Shaw defeated Sky Woodward | 2016 Derby City Classic Bigfoot Challenge 10-Ball |
| Jayson Shaw defeated Sky Woodward | 2020 Derby City Classic Bank Pool |
| Jayson Shaw defeated Sky Woodward | 2020 Derby City Classic 10-Ball |