Monte-Carlo, Monaco, 
)
Madrid, Spain, 
1Grigor Dimitrov (Bulgaria) 3 - 0 Michael Yani (USA)
| Date | Tournament | Surface | Rd | Opp. Rank |
Winner | Score |
|---|---|---|---|---|---|---|
| 27 Jan 2010 |
Honolulu Challenger Honolulu, Hawaii, USA Challenger |
R32 | Grigor Dimitrov (BUL) | 6-2 7-6(3) | ||
| 06 Jan 2010 |
Internationaux de Nouvelle-Calédonie Nouméa, New Caledonia Challenger |
R16 | Grigor Dimitrov (BUL) | 6-3 3-6 6-3 | ||
| 02 Nov 2009 |
Virginia National Bank Champ Charlottesville, Virginia, USA Challenger |
R32 | Grigor Dimitrov (BUL) | 7-5 1-6 7-6(3) |