Viktor Troicki defeated Simone Bolelli 6-3 3-6 7-5 in the Sydney quarter-final on hard. The result followed the form book — Viktor Troicki came in leading the head-to-head 3–2. Viktor Troicki extended the head-to-head to 4–2.
| 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 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.