| Result | Tournament |
|---|---|
| Ben Harrison defeated Kevin O'Leary | 2011 PTC - Event 8 Snooker |
| Darren Bond defeated Kevin O'Leary | 2012 Q School - Event 1 Snooker |
| Ben Harrison defeated Kevin O'Leary | 2012 Q School - Event 2 Snooker |
| Rod Lawler defeated Kevin O'Leary | 2012 Q School - Event 3 Snooker |
| Ben Jones defeated Kevin O'Leary | 2013 Q School - Event 1 Snooker |
| Sydney Wilson defeated Kevin O'Leary | 2013 Q School - Event 2 Snooker |
| Christopher Keogan defeated Kevin O'Leary | 2013 Q School - Event 3 Snooker |