Nikita Kryvonos advanced when Philip Bester retired 3-6 7-6 5-5 in the Canada F3 qualifying round. Nikita Kryvonos extended the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-09-21 | USA F23 | R16 | hard | Philip Bester | 7-6(5) 6-4 |
| 2008-03-10 | Canada F2 | R32 | hard | Nikita Kryvonos | 7-6(5) 3-6 6-4 |
| 2007-09-24 | USA F24 | SF | hard | Nikita Kryvonos | 6-4 6-2 |
| 2006-05-01 | USA F9 | QF | clay | Philip Bester | 6-3 2-6 6-2 |
Averages over each player's completed matches in the selected window (2 vs 49). ATP, WTA & Challenger.
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About