| 19‑Mar‑2025 | Miami | Hard | SF | 5 | 15 | (4)Djokovic vs (14)Grigor Dimitrov [BUL] | Live Scores | | | | | | | | | |
| 30‑Oct‑2023 | Paris Masters | Hard | F | 1 | 17 | (1)Djokovic d. Grigor Dimitrov [BUL] | 6-4 6-3 | (ch) | 1.86 | 12.5% | 2.1% | 66.7% | 81.3% | 68.8% | 0/0 | 1:38 |
| 8‑May‑2023 | Rome Masters | Clay | R32 | 1 | 33 | (1)Djokovic d. (26)Grigor Dimitrov [BUL] | 6-3 4-6 6-1 | | 1.34 | 10.0% | 2.9% | 70.0% | 69.4% | 52.4% | 4/7 | 2:19 |
| 16‑Jan‑2023 | Australian Open | Hard | R32 | 5 | 28 | (4)Djokovic d. (27)Grigor Dimitrov [BUL] | 7-6(7) 6-3 6-4 | (ch) | 1.24 | 9.8% | 1.8% | 72.3% | 74.1% | 41.9% | 5/8 | 3:07 |
| 28‑Oct‑2019 | Paris Masters | Hard | SF | 1 | 27 | (1)Djokovic d. Grigor Dimitrov [BUL] | 7-6(5) 6-4 | (ch) | 1.11 | 8.1% | 6.5% | 64.5% | 85.0% | 63.6% | 0/0 | 1:38 |
| 13‑Aug‑2018 | Cincinnati Masters | Hard | R16 | 10 | 5 | (10)Djokovic d. (5)Grigor Dimitrov [BUL] | 2-6 6-3 6-4 | | 1.05 | 4.7% | 1.2% | 62.8% | 74.1% | 46.9% | 2/5 | 2:19 |
| 18‑Jun‑2018 | Queen's Club | Grass | R16 | 22 | 5 | (WC)Djokovic d. (2)Grigor Dimitrov [BUL] | 6-4 6-1 | (ch) | 1.90 | 5.8% | 7.7% | 65.4% | 88.2% | 55.6% | 1/1 | 1:05 |
| 31‑Oct‑2016 | Paris Masters | Hard | R16 | 1 | 18 | (1)Djokovic d. (14)Grigor Dimitrov [BUL] | 4-6 6-2 6-3 | | 1.19 | 5.3% | 5.3% | 63.8% | 73.3% | 47.1% | 6/8 | 2:23 |
| 29‑Sep‑2014 | Beijing | Hard | QF | 1 | 10 | (1)Djokovic d. (5)Grigor Dimitrov [BUL] | 6-2 6-4 | | 1.36 | 3.2% | 4.8% | 61.9% | 79.5% | 33.3% | 6/8 | 1:30 |
| 23‑Jun‑2014 | Wimbledon | Grass | SF | 2 | 13 | (1)Djokovic d. (11)Grigor Dimitrov [BUL] | 6-4 3-6 7-6(2) 7-6(7) | (ch) | 0.99 | 11.7% | 1.4% | 70.3% | 72.5% | 55.8% | 8/11 | 3:02 |
| 27‑May‑2013 | Roland Garros | Clay | R32 | 1 | 28 | (1)Djokovic d. (26)Grigor Dimitrov [BUL] | 6-2 6-2 6-3 | | 1.87 | 2.8% | 0.0% | 67.6% | 81.3% | 56.5% | 4/5 | 1:44 |
| 5‑May‑2013 | Madrid Masters | Clay | R32 | 1 | 28 | Grigor Dimitrov [BUL] d. (1)Djokovic | 7-6(6) 6-7(8) 6-3 | | 1.00 | 4.0% | 0.0% | 72.0% | 65.6% | 57.1% | 7/11 | 3:06 |
| 7‑Mar‑2013 | Indian Wells Masters | Hard | R32 | 1 | 31 | (1)Djokovic d. (31)Grigor Dimitrov [BUL] | 7-6(4) 6-1 | (ch) | 1.57 | 1.8% | 5.5% | 67.3% | 78.4% | 61.1% | 1/2 | 1:08 |
| 7‑Oct‑2012 | Shanghai Masters | Hard | R32 | 2 | 56 | (2)Djokovic d. Grigor Dimitrov [BUL] | 6-3 6-2 | (ch) | 3.57 | 12.2% | 0.0% | 78.0% | 90.6% | 77.8% | 0/0 | 0:54 |
