| 21‑Sep‑2009 | Metz | Hard | QF | 55 | 13 | (1)Gael Monfils [FRA] d. Tipsarevic | 6-1 4-2 RET | | 0.50 | 5.9% | 2.9% | 73.5% | 56.0% | 33.3% | 1/4 | 0:46 |
| 21‑Sep‑2009 | Metz | Hard | R16 | 55 | 46 | Tipsarevic d. (8)Ivan Ljubicic [CRO] | 6-4 7-6(3) | | 1.29 | 10.1% | 4.3% | 59.4% | 80.5% | 57.1% | 4/5 | 1:55 |
| 21‑Sep‑2009 | Metz | Hard | R32 | 55 | 138 | Tipsarevic d. (LL)Arnaud Clement [FRA] | 6-4 6-4 | | 1.75 | 20.0% | 2.0% | 62.0% | 87.1% | 68.4% | 0/0 | 1:20 |
| 29‑Sep‑2008 | Metz | Hard | QF | 43 | 24 | (4)Paul Henri Mathieu [FRA] d. Tipsarevic | 7-6(4) 6-3 | | 0.80 | 19.7% | 3.0% | 63.6% | 78.6% | 54.2% | 4/5 | 1:37 |
| 29‑Sep‑2008 | Metz | Hard | R16 | 43 | 50 | Tipsarevic d. Ernests Gulbis [LAT] | 6-4 6-4 | | 1.23 | 15.3% | 6.8% | 67.8% | 77.5% | 47.4% | 2/3 | 1:16 |
| 29‑Sep‑2008 | Metz | Hard | R32 | 43 | 83 | Tipsarevic d. (WC)Jeremy Chardy [FRA] | 7-6(5) 7-5 | | 1.24 | 17.9% | 1.2% | 52.4% | 84.1% | 55.0% | 4/4 | 1:55 |
| 1‑Oct‑2007 | Metz | Hard | R32 | 53 | 18 | (3)Andy Murray [GBR] d. Tipsarevic | 6-4 1-6 6-2 | | 0.93 | 11.6% | 2.3% | 58.1% | 76.0% | 44.4% | 12/15 | 1:41 |
