| David Grossman | Sky Woodward | 2 - Wins | 4 - Wins |
|---|
| Match | Tournament |
|---|---|
| Sky Woodward defeated David Grossman | 2013 Derby City Classic Bank Pool |
| Sky Woodward defeated David Grossman | 2014 Derby City Classic 9-Ball |
| Sky Woodward defeated David Grossman | 2020 Derby City Classic Bank Pool |
| Sky Woodward defeated David Grossman | 2020 Derby City Classic One Pocket |
| David Grossman defeated Sky Woodward | 2013 Derby City Classic 9-Ball |
| David Grossman defeated Sky Woodward | 2013 Derby City Classic 9-Ball |