8‑Nov‑1999 | Moscow | Carpet | R32 | 41 | 214 | (Q)Cyril Saulnier [FRA] d. (8)Novak | 2-6 7-6(3) 6-4 | | 0.93 | 4.2% | 2.1% | 53.7% | 60.8% | 45.5% | 2/7 | 2:01 |
1‑Nov‑1999 | Paris Masters | Carpet | R64 | 37 | 32 | Francisco Clavet [ESP] d. Novak | 6-4 6-1 | | 0.75 | 2.2% | 0.0% | 63.0% | 51.7% | 35.3% | 5/10 | 0:56 |
25‑Oct‑1999 | Stuttgart Masters | Hard | R16 | 33 | 4 | (3)Todd Martin [USA] d. Novak | 6-2 6-4 | | 0.63 | 2.2% | 6.5% | 63.0% | 72.4% | 52.9% | 0/3 | 0:54 |
25‑Oct‑1999 | Stuttgart Masters | Hard | R32 | 33 | 16 | Novak d. (14)Cedric Pioline [FRA] | 6-4 3-6 6-3 | | 1.01 | 7.8% | 2.2% | 64.4% | 74.1% | 56.3% | 2/3 | 1:48 |
25‑Oct‑1999 | Stuttgart Masters | Hard | R64 | 33 | 40 | Novak d. Goran Ivanisevic [CRO] | 6-2 3-6 7-6(2) | | 1.44 | 10.5% | 0.0% | 72.4% | 78.2% | 66.7% | 1/3 | 1:25 |
11‑Oct‑1999 | Vienna | Hard | R16 | 34 | 93 | (WC)Roger Federer [SUI] d. Novak | 7-6(8) 6-1 | | 0.76 | 0.0% | 2.8% | 69.0% | 55.1% | 36.4% | 5/10 | 1:11 |
11‑Oct‑1999 | Vienna | Hard | R32 | 34 | 4 | Novak d. (2)Todd Martin [USA] | 7-6(3) 6-7(5) 6-4 | | 1.08 | 4.6% | 0.8% | 64.9% | 60.0% | 56.5% | 12/17 | 2:27 |
4‑Oct‑1999 | Basel | Carpet | R16 | 35 | 12 | (6)Nicolas Kiefer [GER] d. Novak | 6-3 6-7(2) 6-1 | | | | | | | | | |
4‑Oct‑1999 | Basel | Carpet | R32 | 35 | 51 | Novak d. Daniel Vacek [CZE] | 6-4 6-4 | | 1.34 | 8.5% | 3.4% | 64.4% | 78.9% | 61.9% | 1/1 | 1:09 |
24‑Sep‑1999 | Davis Cup WG PO: UZB vs CZE | Hard | RR | 35 | 166 | Novak d. Vadim Kutsenko [RUS] | 6-3 6-3 6-2 | | | | | | | | | |
30‑Aug‑1999 | US Open | Hard | R16 | 41 | 95 | Slava Dosedel [CZE] d. Novak | 6-4 7-5 5-7 7-5 | | 0.90 | 2.7% | 3.4% | 60.1% | 61.8% | 52.5% | 9/16 | 2:37 |
30‑Aug‑1999 | US Open | Hard | R32 | 41 | 38 | Novak d. Fabrice Santoro [FRA] | 6-1 6-0 5-1 RET | | 2.07 | 0.0% | 4.8% | 61.9% | 76.9% | 62.5% | 3/3 | 1:09 |
30‑Aug‑1999 | US Open | Hard | R64 | 41 | 31 | Novak d. Marat Safin [RUS] | 6-2 5-7 6-4 3-6 6-2 | | 1.13 | 3.5% | 1.4% | 61.1% | 75.0% | 51.8% | 8/12 | 2:29 |
30‑Aug‑1999 | US Open | Hard | R128 | 41 | 98 | Novak d. Ramon Delgado [PAR] | 3-6 6-4 6-1 6-0 | | 1.81 | 17.2% | 1.1% | 74.7% | 81.5% | 50.0% | 3/4 | 1:51 |
23‑Aug‑1999 | Long Island | Hard | R32 | 39 | 80 | Bohdan Ulihrach [CZE] d. Novak | 1-6 6-3 6-2 | | 0.89 | 8.0% | 6.9% | 50.6% | 61.4% | 41.9% | 9/14 | 1:37 |
16‑Aug‑1999 | Indianapolis | Hard | R64 | 40 | 165 | (Q)Harel Levy [ISR] d. Novak | 7-5 6-1 | | 0.79 | 6.9% | 3.4% | 72.4% | 54.8% | 43.8% | 2/7 | 1:07 |
9‑Aug‑1999 | Cincinnati Masters | Hard | R16 | 42 | 3 | (3)Andre Agassi [USA] d. Novak | 7-6(3) 7-6(5) | | 0.61 | 9.9% | 6.9% | 56.4% | 77.2% | 40.9% | 8/9 | 1:34 |
9‑Aug‑1999 | Cincinnati Masters | Hard | R32 | 42 | 22 | Novak d. (14)Albert Costa [ESP] | 7-6(3) 7-6(6) | | 1.19 | 9.3% | 2.7% | 62.7% | 85.1% | 39.3% | 2/4 | 1:35 |
9‑Aug‑1999 | Cincinnati Masters | Hard | R64 | 42 | 124 | Novak d. (Q)Axel Pretzsch [GER] | 6-7(3) 7-5 6-3 | | 1.10 | 6.3% | 2.7% | 65.2% | 68.5% | 61.5% | 7/8 | 2:05 |
2‑Aug‑1999 | Canada Masters | Hard | R16 | 41 | 2 | (1)Patrick Rafter [AUS] d. Novak | 6-3 6-4 | | 0.87 | 3.9% | 5.9% | 68.6% | 60.0% | 50.0% | 0/3 | 1:12 |
2‑Aug‑1999 | Canada Masters | Hard | R32 | 41 | 62 | Novak d. Jason Stoltenberg [AUS] | 3-6 6-1 7-6(5) | | 1.12 | 4.2% | 3.2% | 49.5% | 78.7% | 50.0% | 4/6 | 1:49 |
2‑Aug‑1999 | Canada Masters | Hard | R64 | 41 | 37 | Novak d. (16)Jonas Bjorkman [SWE] | 6-2 6-2 | | 1.62 | 11.3% | 5.7% | 69.8% | 70.3% | 68.8% | 0/0 | 0:56 |
19‑Jul‑1999 | Stuttgart Outdoor | Clay | SF | 59 | 49 | Magnus Norman [SWE] d. Novak | 6-1 6-2 | | 0.58 | 2.6% | 0.0% | 50.0% | 47.4% | 42.1% | 2/6 | 0:58 |
19‑Jul‑1999 | Stuttgart Outdoor | Clay | QF | 59 | 11 | Novak d. (3)Marcelo Rios [CHI] | 6-2 6-2 | | 1.31 | 0.0% | 0.0% | 50.0% | 65.2% | 47.8% | 2/4 | 0:53 |
19‑Jul‑1999 | Stuttgart Outdoor | Clay | R16 | 59 | 23 | Novak d. (12)Francisco Clavet [ESP] | 2-6 6-3 6-2 | | 1.05 | 4.6% | 3.4% | 65.5% | 66.7% | 63.3% | 4/6 | 1:27 |
19‑Jul‑1999 | Stuttgart Outdoor | Clay | R32 | 59 | 15 | Novak d. (6)Felix Mantilla [ESP] | 7-5 6-1 | | 3.09 | 23.4% | 0.0% | 55.3% | 92.3% | 76.2% | 0/0 | 0:59 |
19‑Jul‑1999 | Stuttgart Outdoor | Clay | R64 | 59 | 42 | Novak d. Fabrice Santoro [FRA] | 7-6(7) 6-1 | | 1.39 | 1.5% | 1.5% | 59.1% | 74.4% | 51.9% | 1/2 | 1:15 |
5‑Jul‑1999 | Gstaad | Clay | R32 | 58 | 39 | Hicham Arazi [MAR] d. Novak | 6-3 7-6(3) | | 0.85 | 7.9% | 12.7% | 47.6% | 76.7% | 36.4% | 2/5 | 1:12 |
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 |
7‑Jun‑1999 | Halle | Grass | R16 | 49 | 77 | Daniel Vacek [CZE] d. Novak | W/O | | | | | | | | | |
7‑Jun‑1999 | Halle | Grass | R32 | 49 | 93 | Novak d. Bernd Karbacher [GER] | 6-2 6-4 | | 1.77 | 6.3% | 4.2% | 70.8% | 82.4% | 57.1% | 0/0 | 1:00 |
24‑May‑1999 | Roland Garros | Clay | R64 | 49 | 7 | (7)Tim Henman [GBR] d. Novak | 5-7 6-1 7-5 6-2 | | 0.76 | 1.5% | 2.3% | 55.0% | 56.9% | 40.7% | 18/27 | 2:33 |
24‑May‑1999 | Roland Garros | Clay | R128 | 49 | 87 | Novak d. Daniel Nestor [CAN] | 6-2 6-2 6-2 | | 2.13 | 4.7% | 4.7% | 59.4% | 84.2% | 65.4% | 1/1 | 1:13 |
17‑May‑1999 | St. Poelten | Clay | R32 | 48 | 67 | Jan Kroslak [SVK] d. Novak | 7-6(4) 7-5 | | 0.95 | 2.2% | 0.0% | 60.2% | 53.6% | 43.2% | 9/15 | 1:41 |
3‑May‑1999 | Hamburg Masters | Clay | R16 | 54 | 76 | (Q)Arnaud Di Pasquale [FRA] d. Novak | 7-6(6) 7-6(4) | | 1.02 | 1.2% | 3.6% | 56.0% | 68.1% | 48.6% | 3/6 | 1:39 |
3‑May‑1999 | Hamburg Masters | Clay | R32 | 54 | 62 | Novak d. Fernando Meligeni [BRA] | 6-2 3-6 6-1 | | 1.26 | 1.3% | 5.1% | 60.8% | 64.6% | 54.8% | 5/8 | 1:25 |
3‑May‑1999 | Hamburg Masters | Clay | R64 | 54 | 35 | Novak d. Younes El Aynaoui [MAR] | 5-7 6-4 6-1 | | 1.30 | 5.3% | 2.6% | 65.8% | 76.0% | 53.8% | 1/3 | 1:28 |
26‑Apr‑1999 | Prague | Clay | R32 | 55 | 27 | (3)Cedric Pioline [FRA] d. Novak | 7-6(6) 0-6 7-6(4) | | 1.39 | 7.7% | 2.2% | 53.8% | 77.6% | 61.9% | 2/4 | 2:04 |
19‑Apr‑1999 | Monte Carlo Masters | Clay | R16 | 62 | 14 | (10)Albert Costa [ESP] d. (Q)Novak | 4-6 6-2 6-4 | | 0.86 | 3.3% | 5.6% | 62.2% | 67.9% | 44.1% | 11/15 | 1:39 |
19‑Apr‑1999 | Monte Carlo Masters | Clay | R32 | 62 | 12 | (Q)Novak d. (8)Greg Rusedski [GBR] | 6-2 6-2 | | 2.35 | 4.7% | 0.0% | 69.8% | 83.3% | 69.2% | 1/1 | 0:56 |
19‑Apr‑1999 | Monte Carlo Masters | Clay | R64 | 62 | 27 | (Q)Novak d. Marc Rosset [SUI] | 6-3 7-5 | | 1.30 | 0.0% | 1.4% | 62.5% | 71.1% | 70.4% | 5/5 | 1:16 |
12‑Apr‑1999 | Barcelona | Clay | R64 | 65 | 74 | Alberto Martin [ESP] d. Novak | 6-0 6-1 | | 0.50 | 0.0% | 0.0% | 83.3% | 36.0% | 0.0% | 0/5 | 0:47 |
5‑Apr‑1999 | Estoril | Clay | R16 | 65 | 18 | (5)Gustavo Kuerten [BRA] d. Novak | 6-3 6-4 | | 0.79 | 3.2% | 3.2% | 58.1% | 52.8% | 50.0% | 1/5 | 1:12 |
5‑Apr‑1999 | Estoril | Clay | R32 | 65 | 87 | Novak d. Galo Blanco [ESP] | 7-6(1) 6-3 | | 1.29 | 7.2% | 7.2% | 62.3% | 79.1% | 30.8% | 4/7 | 1:41 |
15‑Mar‑1999 | Miami Masters | Hard | R128 | 65 | 54 | Sjeng Schalken [NED] d. Novak | 6-2 6-1 | | 0.46 | 2.0% | 3.9% | 62.7% | 37.5% | 52.6% | 5/10 | 0:52 |
8‑Mar‑1999 | Indian Wells Masters | Hard | R64 | 66 | 31 | Jan Michael Gambill [USA] d. (Q)Novak | 6-2 7-6(3) | | 0.73 | 4.4% | 7.4% | 54.4% | 73.0% | 32.3% | 3/7 | 1:11 |
15‑Feb‑1999 | Memphis | Hard | R16 | 67 | 44 | (12)Andrew Ilie [AUS] d. Novak | 6-4 4-6 6-4 | | 0.87 | 8.8% | 6.9% | 60.8% | 74.2% | 42.5% | 5/8 | 1:46 |
15‑Feb‑1999 | Memphis | Hard | R32 | 67 | 120 | Novak d. (LL)Paul Goldstein [USA] | 6-7(8) 6-0 7-5 | | 1.23 | 6.3% | 3.6% | 60.4% | 73.1% | 56.8% | 6/7 | 1:56 |
15‑Feb‑1999 | Memphis | Hard | R64 | 67 | 91 | Novak d. Sebastien Lareau [CAN] | 7-6(5) 6-7(4) 6-3 | | 1.08 | 8.0% | 2.7% | 58.4% | 75.8% | 55.3% | 4/6 | 1:57 |
18‑Jan‑1999 | Australian Open | Hard | R32 | 73 | 6 | (5)Andre Agassi [USA] d. Novak | 6-3 6-2 6-1 | | 0.49 | 0.0% | 2.6% | 55.3% | 54.8% | 41.2% | 3/9 | 1:18 |
18‑Jan‑1999 | Australian Open | Hard | R64 | 73 | 105 | Novak d. Arnaud Clement [FRA] | 3-6 6-7(1) 6-0 6-3 6-3 | | 1.05 | 4.8% | 3.0% | 65.5% | 67.3% | 46.6% | 13/17 | 3:01 |
18‑Jan‑1999 | Australian Open | Hard | R128 | 73 | 30 | Novak d. Francisco Clavet [ESP] | 6-3 6-4 6-3 | | 1.43 | 3.9% | 0.0% | 73.5% | 65.3% | 63.0% | 6/8 | 1:39 |
4‑Jan‑1999 | Adelaide | Hard | R16 | 75 | 100 | (WC)Lleyton Hewitt [AUS] d. Novak | 7-6(2) 2-6 6-4 | | 0.99 | 3.6% | 2.7% | 70.3% | 69.2% | 39.4% | 7/10 | 2:17 |
4‑Jan‑1999 | Adelaide | Hard | R32 | 75 | 59 | Novak d. Andrew Ilie [AUS] | 6-2 6-1 | | 2.14 | 2.4% | 4.9% | 58.5% | 79.2% | 64.7% | 0/0 | 0:45 |