25‑Oct‑1999 | Brest CH | Hard | R32 | 148 | 241 | (Q)Olivier Mutis [FRA] d. Black | 6-4 6-2 | | | | | | | | | |
18‑Oct‑1999 | Houston CH | Hard | R16 | 117 | 212 | Edwin Kempes [NED] d. (2)Black | 6-4 0-6 7-6(6) | | | | | | | | | |
18‑Oct‑1999 | Houston CH | Hard | R32 | 117 | 201 | (2)Black d. Jeff Coetzee [RSA] | 7-5 6-3 | | | | | | | | | |
11‑Oct‑1999 | Dallas CH | Hard | R32 | 117 | 178 | Harel Levy [ISR] d. (3)Black | 7-6(4) 4-6 7-6(2) | | | | | | | | | |
4‑Oct‑1999 | Tulsa CH | Hard | QF | 120 | 210 | Kevin Kim [USA] d. (3)Black | 6-4 6-2 | | | | | | | | | |
4‑Oct‑1999 | Tulsa CH | Hard | R16 | 120 | 453 | (3)Black d. (Q)Dennis Van Scheppingen [NED] | 6-2 6-1 | | | | | | | | | |
4‑Oct‑1999 | Tulsa CH | Hard | R32 | 120 | 192 | (3)Black d. Jamie Delgado [GBR] | 6-4 6-7(5) 7-5 | | | | | | | | | |
27‑Sep‑1999 | San Antonio CH | Hard | QF | 122 | 235 | Cristiano Caratti [ITA] d. (2)Black | 6-2 6-2 | | | | | | | | | |
27‑Sep‑1999 | San Antonio CH | Hard | R16 | 122 | 217 | (2)Black d. Kevin Kim [USA] | 6-4 7-6(4) | | | | | | | | | |
27‑Sep‑1999 | San Antonio CH | Hard | R32 | 122 | 280 | (2)Black d. (LL)Daniel Melo [BRA] | 0-6 6-3 6-3 | | | | | | | | | |
24‑Sep‑1999 | Davis Cup WG PO: ZIM vs CHI | Hard | RR | 121 | 8 | Black d. Marcelo Rios [CHI] | 7-5 5-7 7-6(3) 7-6(4) | | | | | | | | | |
30‑Aug‑1999 | US Open | Hard | R128 | 117 | 52 | Arnaud Clement [FRA] d. Black | 6-2 6-3 6-4 | | 0.58 | 8.0% | 6.7% | 66.7% | 66.0% | 40.0% | 4/8 | 1:36 |
16‑Aug‑1999 | Washington | Hard | R32 | 112 | 2 | (1)Yevgeny Kafelnikov [RUS] d. Black | 0-6 6-2 6-4 | | 0.97 | 9.5% | 6.8% | 55.4% | 70.7% | 48.5% | 2/5 | 1:21 |
16‑Aug‑1999 | Washington | Hard | R64 | 112 | 108 | Black d. Oliver Gross [GER] | 6-3 6-1 | | 1.64 | 3.3% | 1.6% | 45.9% | 67.9% | 66.7% | 8/8 | 1:07 |
9‑Aug‑1999 | Cincinnati Masters | Hard | R64 | 113 | 93 | John Van Lottum [NED] d. (Q)Black | 6-3 6-2 | | 0.68 | 5.1% | 5.1% | 62.7% | 67.6% | 36.4% | 5/8 | 1:16 |
2‑Aug‑1999 | Canada Masters | Hard | R64 | 104 | 120 | (Q)Max Mirnyi [BLR] d. Black | 7-5 7-5 | | 0.79 | 0.0% | 2.7% | 70.3% | 53.8% | 45.5% | 6/11 | 1:10 |
26‑Jul‑1999 | Los Angeles | Hard | R32 | 103 | 70 | Michael Chang [USA] d. Black | 6-3 6-1 | | 0.63 | 4.4% | 0.0% | 53.3% | 41.7% | 28.6% | 0/6 | 1:08 |
21‑Jun‑1999 | Wimbledon | Grass | R128 | 98 | 100 | Sebastien Lareau [CAN] d. Black | 6-1 3-6 6-3 6-3 | | 0.72 | 1.9% | 3.8% | 66.7% | 64.3% | 42.9% | 5/11 | 1:55 |
14‑Jun‑1999 | Nottingham | Grass | R16 | 96 | 574 | (Q)Kevin Ullyett [ZIM] d. (Q)Black | 6-4 6-2 | | 0.74 | 2.6% | 5.2% | 50.6% | 59.0% | 47.4% | 6/10 | 1:24 |
14‑Jun‑1999 | Nottingham | Grass | R32 | 96 | 273 | (Q)Black d. (Q)Barry Cowan [GBR] | 6-3 6-3 | | 1.55 | 10.9% | 6.5% | 54.3% | 80.0% | 61.9% | 0/1 | 1:07 |
7‑Jun‑1999 | Queen's Club | Grass | R64 | 97 | 45 | (12)Jason Stoltenberg [AUS] d. Black | 6-3 6-4 | | 0.62 | 1.7% | 3.3% | 55.0% | 57.6% | 48.1% | 3/7 | 1:00 |
24‑May‑1999 | Roland Garros | Clay | R128 | 95 | 97 | Alberto Berasategui [ESP] d. Black | 6-0 6-3 4-6 6-2 | | 0.73 | 4.1% | 3.1% | 69.4% | 54.4% | 43.3% | 7/15 | 1:53 |
12‑Apr‑1999 | Tokyo | Hard | R64 | 93 | 55 | (12)Sjeng Schalken [NED] d. Black | 6-4 6-1 | | 0.67 | 1.9% | 5.6% | 70.4% | 44.7% | 43.8% | 2/7 | 1:05 |
5‑Apr‑1999 | Chennai | Hard | R16 | 93 | 2 | (1)Carlos Moya [ESP] d. Black | 6-3 1-6 7-5 | | 1.06 | 2.3% | 2.3% | 58.1% | 58.0% | 58.3% | 2/7 | 1:50 |
5‑Apr‑1999 | Chennai | Hard | R32 | 93 | 115 | Black d. Paul Goldstein [USA] | 7-6(6) 6-1 | | 1.43 | 6.2% | 4.6% | 52.3% | 58.8% | 67.7% | 1/3 | 1:28 |
2‑Apr‑1999 | Davis Cup WG R1: ZIM vs AUS | Hard | RR | 93 | 5 | Patrick Rafter [AUS] d. Black | 6-3 3-6 7-6(4) 6-2 | | | | | | | | | |
2‑Apr‑1999 | Davis Cup WG R1: ZIM vs AUS | Hard | RR | 93 | 9 | Mark Philippoussis [AUS] d. Black | 6-3 6-2 | | | | | | | | | |
15‑Mar‑1999 | Miami Masters | Hard | R64 | 96 | 36 | (32)Jason Stoltenberg [AUS] d. Black | 6-4 1-6 7-6(2) | | 1.05 | 2.9% | 3.8% | 57.1% | 68.3% | 44.4% | 6/11 | 2:09 |
15‑Mar‑1999 | Miami Masters | Hard | R128 | 96 | 73 | Black d. David Prinosil [GER] | 1-6 7-6(7) 6-4 | | 0.99 | 3.7% | 2.8% | 66.4% | 59.2% | 52.8% | 9/14 | 2:20 |
1‑Mar‑1999 | Copenhagen | Carpet | QF | 94 | 32 | (3)Magnus Gustafsson [SWE] d. Black | 6-4 4-6 6-2 | | 0.65 | 1.0% | 0.0% | 58.1% | 62.3% | 45.5% | 5/10 | 2:05 |
1‑Mar‑1999 | Copenhagen | Carpet | R16 | 94 | 48 | Black d. (6)Davide Sanguinetti [ITA] | 7-6(1) 6-3 | | 1.47 | 1.7% | 0.0% | 58.6% | 76.5% | 62.5% | 3/4 | 1:21 |
1‑Mar‑1999 | Copenhagen | Carpet | R32 | 94 | 176 | Black d. Tuomas Ketola [FIN] | 5-7 6-3 6-0 | | 1.32 | 4.3% | 2.9% | 48.6% | 70.6% | 50.0% | 1/5 | 1:43 |
8‑Feb‑1999 | Dubai | Hard | R32 | 88 | 8 | (3)Tim Henman [GBR] d. (Q)Black | 6-0 6-4 | | 0.60 | 6.4% | 2.1% | 61.7% | 58.6% | 44.4% | 1/5 | 1:06 |
18‑Jan‑1999 | Australian Open | Hard | R16 | 97 | 13 | (15)Todd Martin [USA] d. Black | 7-6(3) 6-4 6-4 | | | | | | | | | |
18‑Jan‑1999 | Australian Open | Hard | R32 | 97 | 65 | Black d. Gianluca Pozzi [ITA] | 6-3 4-6 7-5 6-2 | | 1.18 | 1.4% | 2.9% | 67.4% | 72.0% | 42.2% | 7/11 | 3:05 |
18‑Jan‑1999 | Australian Open | Hard | R64 | 97 | 81 | Black d. Andrei Medvedev [UKR] | 6-4 6-4 3-6 4-6 6-2 | | 0.94 | 3.1% | 3.1% | 62.5% | 73.0% | 36.7% | 5/10 | 2:42 |
18‑Jan‑1999 | Australian Open | Hard | R128 | 97 | 71 | Black d. Adrian Voinea [ROU] | 6-2 6-4 6-1 | | 1.54 | 1.3% | 1.3% | 67.1% | 71.7% | 57.7% | 6/7 | 1:29 |