| 13‑May‑2019 | Rome Masters | Clay | R64 | 28 | 56 | Philipp Kohlschreiber [GER] d. Simon | 6-2 3-6 6-3 | | 0.91 | 5.4% | 1.4% | 56.8% | 71.4% | 43.8% | 3/7 | 2:19 |
| 24‑Jul‑2017 | Hamburg | Clay | R16 | 39 | 58 | Philipp Kohlschreiber [GER] d. (4)Simon | 6-3 3-6 6-2 | (ch) | 0.94 | 2.8% | 5.6% | 51.4% | 64.9% | 45.7% | 3/8 | 2:02 |
| 3‑Oct‑2016 | Tokyo | Hard | R32 | 30 | 31 | Simon d. Philipp Kohlschreiber [GER] | 7-5 4-6 6-0 | | 1.44 | 9.5% | 2.4% | 58.3% | 65.3% | 60.0% | 4/8 | 2:09 |
| 6‑Mar‑2015 | Davis Cup WG R1: GER vs FRA | Hard | RR | 14 | 28 | Philipp Kohlschreiber [GER] d. Simon | 7-6(5) 6-4 | | | | | | | | | |
| 14‑Jul‑2014 | Hamburg | Clay | R16 | 38 | 26 | (7)Philipp Kohlschreiber [GER] d. (12)Simon | 7-5 6-3 | | 0.74 | 4.9% | 2.4% | 58.5% | 58.3% | 35.3% | 6/12 | 1:30 |
| 20‑Sep‑2010 | Metz | Hard | SF | 41 | 31 | (8)Simon d. (6)Philipp Kohlschreiber [GER] | 6-3 6-2 | | 2.77 | 19.0% | 0.0% | 69.0% | 89.7% | 76.9% | 0/0 | 0:54 |
| 30‑Aug‑2010 | US Open | Hard | R64 | 42 | 31 | Simon d. (29)Philipp Kohlschreiber [GER] | 4-6 6-3 1-6 6-1 6-3 | | 1.03 | 8.7% | 2.4% | 54.8% | 78.3% | 43.9% | 2/6 | 2:44 |
| 9‑Feb‑2009 | Rotterdam | Hard | R32 | 8 | 38 | (4)Simon d. Philipp Kohlschreiber [GER] | 7-5 7-6(1) | | 1.22 | 9.8% | 1.2% | 52.4% | 90.7% | 43.6% | 6/7 | 1:50 |
| 26‑Feb‑2007 | Dubai | Hard | R32 | 42 | 57 | Simon d. Philipp Kohlschreiber [GER] | 6-4 6-4 | | 1.08 | 4.5% | 1.5% | 60.6% | 62.5% | 57.7% | 5/7 | 1:17 |
| 19‑Feb‑2007 | Rotterdam | Hard | R32 | 42 | 58 | Philipp Kohlschreiber [GER] d. Simon | 6-3 3-1 | | 0.62 | 4.9% | 2.4% | 61.0% | 64.0% | 37.5% | 1/4 | 0:56 |
