Philip Bester defeated Phillip Simmonds 6-4 6-2 in the USA F14 round of 16 on hard. Philip Bester extended the head-to-head to 4–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2012-05-14 | USA F13 | R16 | clay | Philip Bester | 6-4 6-2 |
| 2010-11-15 | USA F31 | R16 | clay | Philip Bester | 6-3 6-3 |
| 2010-11-08 | USA F30 | R16 | clay | Phillip Simmonds | 6-4 6-3 |
| 2009-06-22 | USA F14 | R32 | hard | Philip Bester | 6-7(8) 6-3 7-6(4) |
| 2008-10-13 | USA F26 | R16 | hard | Phillip Simmonds | 7-6(3) 6-3 |
| 2008-02-09 | Delray Beach | Q32 | hard | Phillip Simmonds | 5-7 7-6(4) 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.