| 31‑Oct‑2022 | Paris Masters | Hard | R32 | 28 | 59 | Dimitrov d. (LL)Fabio Fognini [ITA] | 6-0 7-5 | | 1.98 | 10.6% | 0.0% | 61.7% | 86.2% | 55.6% | 1/2 | 1:30 |
| 16‑Oct‑2017 | Stockholm | Hard | SF | 8 | 27 | (1)Dimitrov d. (6)Fabio Fognini [ITA] | 6-3 7-6(2) | (ch) | 1.28 | 11.3% | 1.4% | 69.0% | 69.4% | 59.1% | 3/5 | 1:27 |
| 10‑May‑2015 | Rome Masters | Clay | R32 | 11 | 31 | Fabio Fognini [ITA] d. (10)Dimitrov | 7-6(9) 4-6 6-0 | | 0.90 | 3.2% | 1.1% | 67.4% | 71.9% | 35.5% | 5/10 | 2:18 |
| 3‑May‑2015 | Madrid Masters | Clay | R32 | 11 | 31 | (10)Dimitrov d. Fabio Fognini [ITA] | 3-6 6-2 7-5 | | 1.10 | 2.2% | 1.1% | 73.6% | 65.7% | 50.0% | 11/14 | 2:05 |
| 12‑Apr‑2015 | Monte Carlo Masters | Clay | R32 | 11 | 28 | (9)Dimitrov d. Fabio Fognini [ITA] | 6-3 6-4 | | 1.63 | 7.3% | 0.0% | 74.5% | 82.9% | 57.1% | 1/1 | 1:11 |
| 28‑Oct‑2013 | Paris Masters | Hard | R32 | 22 | 18 | Dimitrov d. (16)Fabio Fognini [ITA] | 6-3 5-7 6-2 | | 1.23 | 8.3% | 4.8% | 56.0% | 76.6% | 32.4% | 6/12 | 1:52 |
| 7‑Jan‑2013 | Sydney | Hard | R32 | 41 | 47 | Fabio Fognini [ITA] d. Dimitrov | 6-3 6-1 | | 0.45 | 8.5% | 6.4% | 53.2% | 72.0% | 27.3% | 3/7 | 0:52 |
