| 5‑Aug‑2024 | Canada Masters | Hard | R32 | 10 | 74 | (7)Dimitrov d. (Q)Rinky Hijikata [AUS] | 6-1 6-0 | | 3.09 | 16.7% | 0.0% | 77.8% | 85.7% | 62.5% | 0/0 | 0:55 |
| 27‑May‑2024 | Roland Garros | Clay | R64 | 10 | 43 | (10)Dimitrov d. Fabian Marozsan [HUN] | 6-0 6-3 6-4 | | 1.72 | 9.9% | 2.8% | 53.5% | 89.5% | 51.5% | 1/2 | |
| 18‑Mar‑2024 | Miami Masters | Hard | R32 | 12 | 56 | (11)Dimitrov d. Yannick Hanfmann [GER] | 6-1 6-0 | (ch) | 4.94 | 6.3% | 3.1% | 71.9% | 91.3% | 77.8% | 0/0 | 0:46 |
| 29‑May‑2023 | Roland Garros | Clay | R128 | 29 | 147 | (28)Dimitrov d. (Q)Timofey Skatov [KAZ] | 6-0 6-3 6-2 | | 1.57 | 11.8% | 3.5% | 63.5% | 77.8% | 41.9% | 4/5 | 1:54 |
| 16‑Jan‑2023 | Australian Open | Hard | R64 | 28 | 68 | (27)Dimitrov d. Laslo Djere [SRB] | 6-3 6-2 6-0 | | 2.31 | 14.5% | 3.2% | 59.7% | 86.5% | 64.0% | 0/0 | 1:34 |
| 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 |
| 22‑Aug‑2022 | Winston-Salem | Hard | R32 | 19 | 231 | (WC)Dominic Thiem [AUT] d. (1)Dimitrov | 0-6 4-2 RET | (ch) | 1.28 | 11.4% | 4.5% | 72.7% | 78.1% | 25.0% | 3/4 | 0:58 |
| 23‑May‑2022 | Roland Garros | Clay | R64 | 21 | 279 | (18)Dimitrov d. Borna Coric [CRO] | 6-0 6-4 6-3 | | 1.78 | 5.3% | 2.7% | 73.3% | 78.2% | 65.0% | 2/2 | |
| 2‑May‑2022 | Madrid Masters | Clay | R32 | 20 | 15 | Dimitrov d. (13)Diego Schwartzman [ARG] | 6-0 6-3 | (ch) | 2.37 | 15.0% | 2.5% | 72.5% | 82.8% | 54.5% | 1/1 | 1:09 |
| 3‑Jan‑2022 | Melbourne | Hard | QF | 28 | 57 | (3)Dimitrov d. Botic Van De Zandschulp [NED] | 6-7(5) 6-0 7-5 | (ch) | 1.49 | 5.6% | 4.5% | 71.9% | 78.1% | 52.0% | 3/5 | 2:44 |
| 1‑Nov‑2021 | Paris Masters | Hard | R32 | 30 | 31 | (16)Dimitrov d. Karen Khachanov [RUS] | 4-6 6-2 6-0 | | 1.54 | 8.3% | 0.0% | 72.2% | 76.9% | 55.0% | 2/3 | 1:55 |
| 8‑Feb‑2021 | Australian Open | Hard | R16 | 21 | 3 | (18)Dimitrov d. (3)Dominic Thiem [AUT] | 6-4 6-4 6-0 | | 1.56 | 13.2% | 1.3% | 68.4% | 71.2% | 58.3% | 5/7 | 2:01 |
| 8‑Feb‑2021 | Australian Open | Hard | R32 | 21 | 16 | (18)Dimitrov d. (15)Pablo Carreno Busta [ESP] | 6-0 1-0 RET | | 2.28 | 16.7% | 0.0% | 55.6% | 90.0% | 50.0% | 1/1 | 0:38 |
| 14‑Sep‑2020 | Rome Masters | Clay | R32 | 22 | 50 | (15)Dimitrov d. Yoshihito Nishioka [JPN] | 6-1 6-0 | | 2.35 | 4.2% | 8.3% | 52.1% | 96.0% | 43.5% | 1/1 | 0:55 |
| 20‑Jan‑2020 | Australian Open | Hard | R128 | 20 | 52 | (18)Dimitrov d. Juan Ignacio Londero [ARG] | 4-6 6-2 6-0 6-4 | | 1.45 | 16.5% | 3.9% | 68.0% | 80.0% | 48.5% | 4/5 | 2:30 |
| 27‑May‑2019 | Roland Garros | Clay | R128 | 46 | 303 | Dimitrov d. Janko Tipsarevic [SRB] | 6-3 6-0 3-6 6-7(4) 6-4 | (ch) | 1.25 | 8.8% | 5.9% | 66.9% | 74.7% | 46.7% | 5/10 | 3:02 |
| 13‑Nov‑2017 | Tour Finals | Hard | SF | 6 | 9 | (6)Dimitrov d. (8)Jack Sock [USA] | 4-6 6-0 6-3 | (ch) | 1.18 | 3.3% | 5.4% | 64.1% | 67.8% | 51.5% | 4/6 | 1:59 |
| 13‑Nov‑2017 | Tour Finals | Hard | RR | 6 | 8 | (6)Dimitrov d. (7)David Goffin [BEL] | 6-0 6-2 | (ch) | 2.03 | 4.3% | 2.1% | 57.4% | 85.2% | 55.0% | 1/1 | |
| 6‑Mar‑2017 | Indian Wells Masters | Hard | R64 | 13 | 84 | (12)Dimitrov d. Mikhail Youzhny [RUS] | 6-4 6-0 | | 2.30 | 16.7% | 2.4% | 59.5% | 88.0% | 58.8% | 0/1 | 1:10 |
| 29‑Jun‑2015 | Wimbledon | Grass | R128 | 11 | 73 | (11)Dimitrov d. Federico Delbonis [ARG] | 6-3 6-0 6-4 | | 2.63 | 9.1% | 3.0% | 53.0% | 91.4% | 71.0% | 2/2 | |
| 23‑Feb‑2015 | Acapulco | Hard | R32 | 10 | 101 | (3)Dimitrov d. Filip Krajinovic [SRB] | 6-3 5-7 6-0 | | 1.38 | 6.2% | 7.4% | 56.8% | 71.7% | 45.7% | 2/7 | 2:02 |
| 27‑Oct‑2014 | Paris Masters | Hard | R32 | 11 | 34 | (9)Dimitrov d. Pablo Cuevas [URU] | 6-0 6-3 | | 1.65 | 10.9% | 1.8% | 56.4% | 80.6% | 54.2% | 2/2 | 1:02 |
| 4‑Apr‑2014 | Davis Cup G2 PO: GRE vs BUL | Clay | RR | 15 | 690 | Dimitrov d. Markos Kalovelonis [GRE] | 6-3 6-3 6-0 | | | | | | | | | |
| 1‑Feb‑2013 | Davis Cup G2 R1: BUL vs FIN | Hard | RR | 40 | 1117 | Dimitrov d. Juho Paukku [FIN] | 6-1 6-1 6-0 | | | | | | | | | |
| 1‑Feb‑2013 | Davis Cup G2 R1: BUL vs FIN | Hard | RR | 40 | 949 | Dimitrov d. Micke Kontinen [FIN] | 6-0 6-3 6-1 | | | | | | | | | |
| 4‑Apr‑2011 | Houston | Clay | R32 | 70 | 87 | (8)Dimitrov d. Rainer Schuettler [GER] | 6-0 6-2 | | 1.65 | 4.7% | 2.3% | 58.1% | 84.0% | 38.9% | 4/5 | 1:04 |
| 28‑Feb‑2011 | Cherbourg CH | Hard | SF | 78 | 205 | (1)Dimitrov d. Stephane Robert [FRA] | 6-3 6-0 | | 1.68 | 6.5% | 1.6% | 50.0% | 83.9% | 45.2% | 5/6 | 1:07 |
| 21‑Feb‑2011 | Dubai | Hard | Q1 | 81 | | (3)Dimitrov d. (WC)Mahmoud Nader Al Baloushi [UAE] | 6-0 6-3 | | 1.73 | 4.7% | 4.7% | 67.4% | 82.8% | 42.9% | 3/3 | 0:52 |
| 22‑Nov‑2010 | Helsinki CH | Hard | SF | 112 | 119 | Ricardas Berankis [LTU] d. Dimitrov | 7-6(5) 0-6 6-1 | | 0.99 | 9.3% | 2.3% | 51.2% | 75.0% | 50.0% | 4/6 | 1:52 |
| 11‑Oct‑2010 | Rennes CH | Hard | R32 | 136 | 252 | (7)Dimitrov d. (WC)Laurent Rochette [FRA] | 1-6 6-0 6-4 | | 0.97 | 9.9% | 8.6% | 55.6% | 57.8% | 63.9% | 8/11 | 1:27 |
| 13‑Sep‑2010 | Bangkok CH | Hard | SF | 190 | 110 | (7)Dimitrov d. (2)Go Soeda [JPN] | 6-3 6-7(3) 6-0 | | 1.04 | 3.6% | 2.7% | 65.5% | 73.6% | 44.7% | 8/9 | 2:20 |
| 13‑Sep‑2010 | Bangkok CH | Hard | R32 | 190 | 354 | (7)Dimitrov d. (Q)Woong Sun Jun [KOR] | 2-6 6-0 6-1 | | 1.55 | 3.2% | 4.8% | 52.4% | 84.8% | 50.0% | 2/4 | 1:36 |
| 21‑Sep‑2009 | Trnava CH | Clay | R32 | 290 | 212 | Dimitrov d. Kamil Capkovic [SVK] | 6-3 6-0 | | | | | | | | | |
| 16‑Mar‑2009 | Bangkok CH | Hard | R32 | 400 | 1337 | (WC)Dimitrov d. (WC)Peerakit Siributwong [THA] | 6-0 6-3 | | | | | | | | | |
| 6‑Mar‑2009 | Davis Cup G2 R1: HUN vs BUL | Carpet | RR | 402 | 307 | Dimitrov d. Attila Balazs [HUN] | 7-6(2) 3-6 6-3 3-6 6-0 | | | | | | | | | |
| 26‑May‑2008 | Spain F21 | Clay | R32 | 1049 | 1494 | Dimitrov d. (WC)David Costa Soria [ESP] | 6-0 6-0 | | | | | | | | | |
| 19‑May‑2008 | Spain F20 | Clay | R32 | 1046 | 510 | (Q)Dimitrov d. (8)Pedro Clar Rossello [ESP] | 6-0 6-7(5) 6-1 | | | | | | | | | |
| 12‑Nov‑2007 | Spain F41 | Clay | R16 | | 608 | (Q)Dimitrov d. (6)Dusan Karol [CZE] | 7-5 6-7(4) 6-0 | | | | | | | | | |
