| 26‑Jun‑2006 | Wimbledon | Grass | R128 | 110 | 34 | (30)Kristof Vliegen [BEL] d. Novak | 6-4 7-5 6-2 | | 0.63 | 8.2% | 2.1% | 72.2% | 61.4% | 51.9% | 4/8 | 1:47 |
| 20‑Jun‑2005 | Wimbledon | Grass | R32 | 28 | 36 | Max Mirnyi [BLR] d. (28)Novak | 5-7 7-5 6-4 7-6(2) | | 0.72 | 5.4% | 0.7% | 73.2% | 65.1% | 57.5% | 6/10 | 2:43 |
| 20‑Jun‑2005 | Wimbledon | Grass | R64 | 28 | 53 | (28)Novak d. Fabrice Santoro [FRA] | 6-1 4-6 7-6(4) 6-3 | | 1.09 | 5.8% | 1.9% | 69.2% | 67.6% | 54.2% | 20/23 | 2:43 |
| 20‑Jun‑2005 | Wimbledon | Grass | R128 | 28 | 79 | (28)Novak d. Peter Wessels [NED] | 7-6(4) 6-3 6-4 | | 1.02 | 8.4% | 0.8% | 77.3% | 59.8% | 66.7% | 7/10 | 1:38 |
| 21‑Jun‑2004 | Wimbledon | Grass | R128 | 16 | 51 | Xavier Malisse [BEL] d. (16)Novak | 6-3 6-4 6-4 | | 0.55 | 2.1% | 4.2% | 72.6% | 66.7% | 30.8% | 3/7 | 1:30 |
| 23‑Jun‑2003 | Wimbledon | Grass | R32 | 10 | 198 | Alexander Popp [GER] d. (11)Novak | 6-3 6-4 7-6(3) | | 0.64 | 0.0% | 1.1% | 81.1% | 58.4% | 61.1% | 1/5 | 1:34 |
| 23‑Jun‑2003 | Wimbledon | Grass | R64 | 10 | 64 | (11)Novak d. David Ferrer [ESP] | 6-2 7-5 6-3 | | 1.37 | 2.4% | 2.4% | 70.2% | 72.9% | 40.0% | 3/6 | 1:29 |
| 23‑Jun‑2003 | Wimbledon | Grass | R128 | 10 | 114 | (11)Novak d. Luis Horna [PER] | 3-6 7-6(1) 6-1 6-1 | | 1.34 | 12.9% | 2.0% | 76.2% | 74.0% | 45.8% | 3/6 | 2:01 |
| 24‑Jun‑2002 | Wimbledon | Grass | R64 | 12 | 89 | Wayne Arthurs [AUS] d. (12)Novak | 6-3 7-6(9) 6-3 | | 0.78 | 4.7% | 3.5% | 72.1% | 80.6% | 41.7% | 3/5 | 1:31 |
| 24‑Jun‑2002 | Wimbledon | Grass | R128 | 12 | 60 | (12)Novak d. Fernando Meligeni [BRA] | 2-6 6-0 6-4 6-4 | | 1.30 | 5.9% | 5.9% | 68.3% | 68.1% | 56.3% | 2/5 | 2:02 |
| 25‑Jun‑2001 | Wimbledon | Grass | R64 | 42 | 34 | (23)Todd Martin [USA] d. Novak | 6-7(3) 2-6 6-4 6-4 6-4 | | 1.08 | 8.0% | 3.6% | 72.5% | 73.0% | 47.4% | 5/11 | 2:36 |
| 25‑Jun‑2001 | Wimbledon | Grass | R128 | 42 | 58 | Novak d. Fernando Vicente [ESP] | 6-1 6-4 6-3 | | 1.71 | 5.8% | 5.8% | 68.1% | 76.6% | 63.6% | 0/1 | 1:11 |
| 26‑Jun‑2000 | Wimbledon | Grass | R128 | 45 | 64 | Gianluca Pozzi [ITA] d. Novak | 6-3 6-4 3-6 6-1 | | 0.73 | 1.9% | 2.9% | 71.8% | 68.9% | 48.3% | 2/6 | 1:56 |
| 21‑Jun‑1999 | Wimbledon | Grass | R64 | 59 | 14 | (8)Todd Martin [USA] d. Novak | 7-6(5) 6-4 6-4 | | 0.77 | 5.5% | 1.8% | 78.2% | 65.1% | 58.3% | 5/8 | 1:39 |
| 21‑Jun‑1999 | Wimbledon | Grass | R128 | 59 | 103 | Novak d. (WC)Roger Federer [SUI] | 6-3 3-6 4-6 6-3 6-4 | | 0.93 | 0.6% | 2.9% | 76.0% | 65.4% | 39.0% | 17/21 | 2:18 |
| 22‑Jun‑1998 | Wimbledon | Grass | R128 | 71 | 18 | (12)Tim Henman [GBR] d. Novak | 7-6(4) 7-5 5-7 4-6 6-2 | | 0.73 | 2.2% | 4.0% | 64.8% | 63.3% | 45.0% | 20/26 | 3:10 |
| 23‑Jun‑1997 | Wimbledon | Grass | R128 | 60 | 144 | Frederik Fetterlein [DEN] d. Novak | 4-6 3-6 6-4 7-6(3) 6-4 | | 0.87 | 3.3% | 2.8% | 73.3% | 69.7% | 33.3% | 12/18 | 2:45 |
| 24‑Jun‑1996 | Wimbledon | Grass | R64 | 44 | 46 | Jason Stoltenberg [AUS] d. Novak | 7-6(5) 6-1 6-1 | | 0.60 | 1.0% | 5.0% | 70.0% | 50.0% | 26.7% | 7/14 | 1:35 |
| 24‑Jun‑1996 | Wimbledon | Grass | R128 | 44 | 174 | Novak d. (Q)Joern Renzenbrink [GER] | 7-6(5) 6-2 6-4 | | 1.54 | 8.0% | 3.6% | 65.2% | 79.5% | 53.8% | 4/5 | 1:44 |