Grigor Dimitrov (Bulgaria) 0 - 3 Ilija Bozoljac (Serbia)
| Date | Tournament | Rnd | Winner | Score |
|---|---|---|---|---|
| 02 Nov 2010 |
Bauer Cup
Eckental,
Germany
Challenger, Carpet |
R32 |
Ilija Bozoljac
(SRB  )
|
4-6 6-7(4) |
| 09 Nov 2009 |
Knoxville Challenger
Knoxville, Tennessee,
USA
Challenger, Hard |
R32 |
Ilija Bozoljac
(SRB )
|
4-6 4-6 |
| 05 Jun 2009 |
AEGON Trophy
Nottingham,
Great Britain
Challenger, Grass |
Q |
Ilija Bozoljac
(SRB )
|
6-1 3-6 4-6 |