Monte-Carlo, Monaco, 
)
Madrid, Spain, 
1Grigor Dimitrov (Bulgaria) 0 - 3 Ilija Bozoljac (Serbia)
| Date | Tournament | Surface | Rd | Opp. Rank |
Winner | Score |
|---|---|---|---|---|---|---|
| 02 Nov 2010 |
Bauer Cup Eckental, Germany Challenger |
R32 | Ilija Bozoljac (SRB) | 4-6 6-7(4) | ||
| 09 Nov 2009 |
Knoxville Challenger Knoxville, Tennessee, USA Challenger |
R32 | Ilija Bozoljac (SRB) | 4-6 4-6 | ||
| 05 Jun 2009 |
AEGON Trophy Nottingham, Great Britain Challenger |
Q | Ilija Bozoljac (SRB) | 6-1 3-6 4-6 |