| 13‑Jan‑2025 | Australian Open | Hard | SF | 7 | 2 | (2)Alexander Zverev [GER] d. (7)Djokovic | 7-6(5) 0-0 RET | (ch) | 0.55 | 9.3% | 0.0% | 53.7% | 72.4% | 60.0% | 5/5 | 1:21 |
| 26‑Aug‑2024 | US Open | Hard | R32 | 2 | 28 | (28)Alexei Popyrin [AUS] d. (2)Djokovic | 6-4 6-4 2-6 6-4 | (ch) | 0.96 | 12.3% | 10.8% | 58.5% | 71.1% | 46.3% | 7/12 | 3:19 |
| 1‑Jul‑2024 | Wimbledon | Grass | F | 2 | 3 | (3)Carlos Alcaraz [ESP] d. (2)Djokovic | 6-2 6-2 7-6(4) | (ch) | 0.71 | 7.9% | 4.0% | 70.3% | 66.2% | 40.0% | 9/14 | 2:27 |
| 15‑Jan‑2024 | Australian Open | Hard | SF | 1 | 4 | (4)Jannik Sinner [ITA] d. (1)Djokovic | 6-1 6-2 6-7(6) 6-3 | (ch) | 0.64 | 6.0% | 3.4% | 68.1% | 67.1% | 45.9% | 6/11 | 3:22 |
| 3‑Jul‑2023 | Wimbledon | Grass | F | 2 | 1 | (1)Carlos Alcaraz [ESP] d. (2)Djokovic | 1-6 7-6(6) 6-1 3-6 6-4 | (ch) | 0.93 | 1.1% | 1.6% | 64.1% | 61.9% | 56.1% | 14/19 | 4:43 |
| 23‑May‑2022 | Roland Garros | Clay | QF | 1 | 5 | (5)Rafael Nadal [ESP] d. (1)Djokovic | 6-2 4-6 6-2 7-6(4) | (ch) | 0.85 | 3.6% | 2.9% | 69.3% | 63.9% | 41.9% | 10/17 | 4:12 |
| 30‑Aug‑2021 | US Open | Hard | F | 1 | 2 | (2)Daniil Medvedev [RUS] d. (1)Djokovic | 6-4 6-4 6-4 | (ch) | 0.76 | 6.5% | 3.3% | 54.3% | 80.0% | 40.5% | 4/8 | 2:16 |
| 28‑Sep‑2020 | Roland Garros | Clay | F | 1 | 2 | (1)Rafael Nadal [ESP] d. (2)Djokovic | 6-0 6-2 7-5 | (ch) | 0.66 | 1.0% | 4.0% | 66.7% | 50.0% | 48.5% | 11/18 | 2:41 |
| 31‑Aug‑2020 | US Open | Hard | R16 | 1 | 27 | (20)Pablo Carreno Busta [ESP] d. (1)Djokovic | 6-5 DEF | | 1.33 | 32.1% | 0.0% | 71.4% | 80.0% | 62.5% | 1/2 | 1:00 |
| 26‑Aug‑2019 | US Open | Hard | R16 | 1 | 24 | (23)Stan Wawrinka [SUI] d. (1)Djokovic | 6-4 7-5 2-1 RET | (ch) | 0.70 | 2.7% | 6.8% | 60.3% | 70.5% | 41.4% | 3/7 | 1:46 |
| 27‑May‑2019 | Roland Garros | Clay | SF | 1 | 4 | (4)Dominic Thiem [AUT] d. (1)Djokovic | 6-2 3-6 7-5 5-7 7-5 | (ch) | 0.90 | 3.4% | 2.3% | 75.1% | 62.4% | 47.7% | 13/22 | 4:13 |
| 28‑May‑2018 | Roland Garros | Clay | QF | 22 | 72 | Marco Cecchinato [ITA] d. (20)Djokovic | 6-3 7-6(4) 1-6 7-6(11) | (ch) | 1.10 | 3.9% | 1.6% | 68.5% | 65.5% | 55.0% | 6/10 | 3:26 |
| 15‑Jan‑2018 | Australian Open | Hard | R16 | 14 | 58 | Hyeon Chung [KOR] d. (14)Djokovic | 7-6(4) 7-5 7-6(3) | | 0.92 | 1.5% | 6.9% | 62.3% | 65.4% | 38.8% | 4/10 | 3:21 |
| 3‑Jul‑2017 | Wimbledon | Grass | QF | 4 | 15 | (11)Tomas Berdych [CZE] d. (2)Djokovic | 7-6(2) 2-0 RET | | 0.62 | 2.1% | 0.0% | 83.0% | 64.1% | 50.0% | 0/1 | 1:03 |
| 29‑May‑2017 | Roland Garros | Clay | QF | 2 | 7 | (6)Dominic Thiem [AUT] d. (2)Djokovic | 7-6(5) 6-3 6-0 | (ch) | 0.70 | 1.9% | 2.9% | 64.4% | 56.7% | 40.5% | 9/15 | 2:15 |
| 16‑Jan‑2017 | Australian Open | Hard | R64 | 2 | 117 | Denis Istomin [UZB] d. (2)Djokovic | 7-6(8) 5-7 2-6 7-6(5) 6-4 | (ch) | 1.07 | 7.6% | 4.9% | 57.8% | 72.0% | 55.1% | 10/14 | 4:48 |
| 29‑Aug‑2016 | US Open | Hard | F | 1 | 3 | (3)Stan Wawrinka [SUI] d. (1)Djokovic | 6-7(1) 6-4 7-5 6-3 | (ch) | 1.11 | 4.9% | 5.7% | 51.2% | 77.8% | 53.3% | 4/10 | 3:54 |
| 27‑Jun‑2016 | Wimbledon | Grass | R32 | 1 | 41 | (28)Sam Querrey [USA] d. (1)Djokovic | 7-6(6) 6-1 3-6 7-6(5) | (ch) | 0.91 | 4.8% | 1.4% | 66.4% | 64.9% | 55.1% | 11/15 | 2:56 |
| 24‑May‑2015 | Roland Garros | Clay | F | 1 | 9 | (8)Stan Wawrinka [SUI] d. (1)Djokovic | 4-6 6-4 6-3 6-4 | (ch) | 0.80 | 4.7% | 0.0% | 64.8% | 62.7% | 53.3% | 11/15 | 3:12 |
| 25‑Aug‑2014 | US Open | Hard | SF | 1 | 11 | (10)Kei Nishikori [JPN] d. (1)Djokovic | 6-4 1-6 7-6(4) 6-3 | (ch) | 1.07 | 13.4% | 3.6% | 58.9% | 80.3% | 37.0% | 2/7 | 2:52 |
| 26‑May‑2014 | Roland Garros | Clay | F | 2 | 1 | (1)Rafael Nadal [ESP] d. (2)Djokovic | 3-6 7-5 6-2 6-4 | (ch) | 0.84 | 8.7% | 2.4% | 65.1% | 72.0% | 36.4% | 4/10 | 3:31 |
| 13‑Jan‑2014 | Australian Open | Hard | QF | 2 | 8 | (8)Stan Wawrinka [SUI] d. (2)Djokovic | 2-6 6-4 6-2 3-6 9-7 | (ch) | 1.16 | 4.9% | 0.7% | 72.9% | 71.4% | 59.0% | 5/10 | 4:00 |
| 26‑Aug‑2013 | US Open | Hard | F | 1 | 2 | (2)Rafael Nadal [ESP] d. (1)Djokovic | 6-2 3-6 6-4 6-1 | (ch) | 0.84 | 5.9% | 2.0% | 67.6% | 58.0% | 48.5% | 5/11 | 3:21 |
| 24‑Jun‑2013 | Wimbledon | Grass | F | 1 | 2 | (2)Andy Murray [GBR] d. (1)Djokovic | 6-4 7-5 6-4 | (ch) | 0.82 | 3.8% | 3.8% | 64.8% | 58.8% | 40.5% | 10/17 | 3:09 |
| 27‑May‑2013 | Roland Garros | Clay | SF | 1 | 4 | (3)Rafael Nadal [ESP] d. (1)Djokovic | 6-4 3-6 6-1 6-7(3) 9-7 | (ch) | 0.82 | 2.9% | 1.1% | 67.4% | 64.4% | 52.6% | 8/16 | 4:37 |
| 27‑Aug‑2012 | US Open | Hard | F | 2 | 4 | (3)Andy Murray [GBR] d. (2)Djokovic | 7-6(10) 7-5 2-6 3-6 6-2 | (ch) | 0.95 | 4.2% | 3.0% | 62.4% | 63.1% | 41.9% | 8/15 | 4:54 |
| 25‑Jun‑2012 | Wimbledon | Grass | SF | 1 | 3 | (3)Roger Federer [SUI] d. (1)Djokovic | 6-3 3-6 6-4 6-3 | (ch) | 0.76 | 7.8% | 1.7% | 63.5% | 71.2% | 57.1% | 8/11 | 2:19 |
| 27‑May‑2012 | Roland Garros | Clay | F | 1 | 2 | (2)Rafael Nadal [ESP] d. (1)Djokovic | 6-4 6-3 2-6 7-5 | (ch) | 0.91 | 2.4% | 3.3% | 59.3% | 61.6% | 44.0% | 8/17 | 3:49 |
| 22‑May‑2011 | Roland Garros | Clay | SF | 2 | 3 | (3)Roger Federer [SUI] d. (2)Djokovic | 7-6(5) 6-3 3-6 7-6(5) | (ch) | 0.82 | 4.2% | 1.2% | 66.7% | 59.8% | 60.7% | 21/25 | 3:39 |
| 30‑Aug‑2010 | US Open | Hard | F | 3 | 1 | (1)Rafael Nadal [ESP] d. (3)Djokovic | 6-4 5-7 6-4 6-2 | (ch) | 0.77 | 3.5% | 2.8% | 65.7% | 64.9% | 44.9% | 20/25 | 3:43 |
| 21‑Jun‑2010 | Wimbledon | Grass | SF | 3 | 13 | (12)Tomas Berdych [CZE] d. (3)Djokovic | 6-3 7-6(9) 6-3 | (ch) | 0.75 | 10.2% | 9.1% | 72.7% | 73.4% | 41.7% | 4/7 | 2:18 |
| 24‑May‑2010 | Roland Garros | Clay | QF | 3 | 27 | (22)Jurgen Melzer [AUT] d. (3)Djokovic | 3-6 2-6 6-2 7-6(3) 6-4 | | 0.88 | 2.0% | 5.1% | 64.5% | 66.9% | 45.7% | 20/24 | 4:15 |
| 18‑Jan‑2010 | Australian Open | Hard | QF | 3 | 10 | (10)Jo Wilfried Tsonga [FRA] d. (3)Djokovic | 7-6(8) 6-7(5) 1-6 6-3 6-1 | (ch) | 1.02 | 1.4% | 6.2% | 69.0% | 67.0% | 48.9% | 4/11 | 3:52 |
| 31‑Aug‑2009 | US Open | Hard | SF | 4 | 1 | (1)Roger Federer [SUI] d. (4)Djokovic | 7-6(3) 7-5 7-5 | (ch) | 0.80 | 5.2% | 3.5% | 67.8% | 67.9% | 54.1% | 7/10 | 2:34 |
| 22‑Jun‑2009 | Wimbledon | Grass | QF | 4 | 34 | (24)Tommy Haas [GER] d. (4)Djokovic | 7-5 7-6(6) 4-6 6-3 | (ch) | 0.89 | 10.5% | 3.2% | 58.9% | 79.5% | 54.9% | 2/5 | 2:45 |
| 25‑May‑2009 | Roland Garros | Clay | R32 | 4 | 31 | (29)Philipp Kohlschreiber [GER] d. (4)Djokovic | 6-4 6-4 6-4 | | 0.82 | 3.3% | 3.3% | 64.4% | 65.5% | 40.6% | 5/10 | 2:21 |
| 19‑Jan‑2009 | Australian Open | Hard | QF | 3 | 9 | (7)Andy Roddick [USA] d. (3)Djokovic | 6-7(3) 6-4 6-2 2-1 RET | (ch) | 0.59 | 7.0% | 4.3% | 62.6% | 63.9% | 46.5% | 7/12 | 2:30 |
| 25‑Aug‑2008 | US Open | Hard | SF | 3 | 2 | (2)Roger Federer [SUI] d. (3)Djokovic | 6-3 5-7 7-5 6-2 | (ch) | 0.78 | 4.8% | 4.0% | 64.5% | 71.3% | 45.5% | 7/12 | 2:44 |
| 23‑Jun‑2008 | Wimbledon | Grass | R64 | 3 | 75 | Marat Safin [RUS] d. (3)Djokovic | 6-4 7-6(3) 6-2 | (ch) | 0.71 | 4.1% | 10.3% | 64.9% | 73.0% | 35.3% | 8/12 | 2:02 |
| 25‑May‑2008 | Roland Garros | Clay | SF | 3 | 2 | (2)Rafael Nadal [ESP] d. (3)Djokovic | 6-4 6-2 7-6(3) | (ch) | 0.78 | 2.0% | 1.0% | 54.0% | 57.4% | 58.7% | 9/14 | 2:49 |
| 27‑Aug‑2007 | US Open | Hard | F | 3 | 1 | (1)Roger Federer [SUI] d. (3)Djokovic | 7-6(4) 7-6(2) 6-4 | (ch) | 0.76 | 4.3% | 6.0% | 55.2% | 70.3% | 55.8% | 2/5 | 2:24 |
| 25‑Jun‑2007 | Wimbledon | Grass | SF | 5 | 2 | (2)Rafael Nadal [ESP] d. (4)Djokovic | 3-6 6-1 4-1 RET | (ch) | 0.72 | 9.1% | 2.6% | 64.9% | 66.0% | 40.7% | 6/10 | 1:41 |
| 28‑May‑2007 | Roland Garros | Clay | SF | 6 | 2 | (2)Rafael Nadal [ESP] d. (6)Djokovic | 7-5 6-4 6-2 | (ch) | 0.62 | 3.2% | 1.1% | 71.6% | 57.4% | 37.0% | 3/9 | 2:28 |
| 15‑Jan‑2007 | Australian Open | Hard | R16 | 15 | 1 | (1)Roger Federer [SUI] d. (14)Djokovic | 6-2 7-5 6-3 | (ch) | 0.56 | 6.9% | 2.0% | 61.4% | 61.3% | 46.2% | 3/8 | 1:50 |
| 28‑Aug‑2006 | US Open | Hard | R32 | 23 | 17 | (15)Lleyton Hewitt [AUS] d. (20)Djokovic | 6-3 6-1 6-2 | | 0.54 | 3.6% | 8.4% | 67.5% | 57.1% | 37.0% | 5/11 | 1:29 |
| 26‑Jun‑2006 | Wimbledon | Grass | R16 | 39 | 10 | (7)Mario Ancic [CRO] d. Djokovic | 6-4 4-6 4-6 7-5 6-3 | | 0.96 | 8.3% | 3.8% | 65.2% | 81.4% | 54.3% | 5/8 | 3:24 |
| 29‑May‑2006 | Roland Garros | Clay | QF | 63 | 2 | (2)Rafael Nadal [ESP] d. Djokovic | 6-4 6-4 RET | (ch) | 0.69 | 3.0% | 4.5% | 73.1% | 55.1% | 22.2% | 2/7 | 1:54 |
| 16‑Jan‑2006 | Australian Open | Hard | R128 | 76 | 68 | Paul Goldstein [USA] d. Djokovic | 6-2 1-6 6-3 6-2 | | 0.85 | 5.3% | 7.9% | 62.3% | 62.0% | 41.9% | 13/19 | 2:28 |
| 29‑Aug‑2005 | US Open | Hard | R32 | 97 | 48 | Fernando Verdasco [ESP] d. Djokovic | 6-1 4-6 6-7(2) 6-4 6-4 | | 0.84 | 3.2% | 1.9% | 68.8% | 62.3% | 54.2% | 6/14 | 3:04 |
| 20‑Jun‑2005 | Wimbledon | Grass | R32 | 128 | 27 | (9)Sebastien Grosjean [FRA] d. (Q)Djokovic | 7-5 6-4 5-7 6-4 | | 1.04 | 4.8% | 3.2% | 69.8% | 75.0% | 55.3% | 6/9 | 2:51 |
| 23‑May‑2005 | Roland Garros | Clay | R64 | 153 | 9 | (8)Guillermo Coria [ARG] d. (Q)Djokovic | 4-6 6-2 3-2 RET | | 0.88 | 3.8% | 3.8% | 52.5% | 54.8% | 44.7% | 5/11 | 1:54 |
| 17‑Jan‑2005 | Australian Open | Hard | R128 | 188 | 4 | (4)Marat Safin [RUS] d. (Q)Djokovic | 6-0 6-2 6-1 | (ch) | 0.37 | 1.5% | 7.6% | 59.1% | 41.0% | 18.5% | 4/13 | 1:14 |
