Grigor Dimitrov (Bulgaria) 0 - 1 Nikola Mektic (Croatia)
| Date | Tournament | Rnd | Winner | Score |
|---|---|---|---|---|
| 19 Jul 2009 |
Guzzini Challenger
Recanati,
Italy
Challenger, Hard |
Q-R16 |
Nikola Mektic
(CRO  )
|
4-6 2-6 |