Viktor Troicki defeated Simone Bolelli 6-3 3-6 7-5 in the Sydney quarter-final on hard. Viktor Troicki extended the head-to-head to 4–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2017-10-16 | Stockholm | R32 | hard | Viktor Troicki | 6-3 6-3 |
| 2015-05-24 | Roland Garros | R64 | clay | Simone Bolelli | 6-2 6-4 6-3 |
| 2015-03-25 | Miami Masters | R64 | hard | Viktor Troicki | 7-5 3-6 6-4 |
| 2009-02-23 | Dubai | R32 | hard | Simone Bolelli | 6-3 6-4 |
| 2009-02-02 | Zagreb | R32 | hard | Viktor Troicki | 6-3 6-4 |
| 2006-10-21 | Basel | Q32 | hard | Simone Bolelli | 6-7(4) 7-6(3) 6-1 |
Averages over each player's completed matches in the selected window (200 vs 180). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About