| 8‑Nov‑1999 | Moscow | Carpet | F | 80 | 2 | (1)Yevgeny Kafelnikov [RUS] d. Black | 7-6(2) 6-4 | | 0.82 | 13.6% | 4.9% | 56.8% | 69.6% | 48.6% | 7/9 | 1:31 |
| 8‑Nov‑1999 | Moscow | Carpet | SF | 80 | 73 | Black d. Jeff Tarango [USA] | 6-3 6-2 | | 2.32 | 25.6% | 4.7% | 53.5% | 91.3% | 60.0% | 1/2 | 0:59 |
| 8‑Nov‑1999 | Moscow | Carpet | QF | 80 | 38 | Black d. Fabrice Santoro [FRA] | 6-3 6-4 | | 1.24 | 15.4% | 6.2% | 50.8% | 72.7% | 40.6% | 3/6 | 1:15 |
| 8‑Nov‑1999 | Moscow | Carpet | R16 | 80 | 47 | Black d. Goran Ivanisevic [CRO] | 7-6(4) 3-1 RET | | 1.76 | 20.0% | 0.0% | 53.3% | 87.5% | 76.2% | 0/0 | 0:55 |
| 8‑Nov‑1999 | Moscow | Carpet | R32 | 80 | 40 | Black d. Hicham Arazi [MAR] | 6-1 7-5 | | 1.23 | 1.4% | 5.5% | 53.4% | 74.4% | 50.0% | 6/7 | 1:07 |
| 11‑Oct‑1999 | Singapore | Hard | R32 | 82 | 142 | (Q)Mikael Tillstrom [SWE] d. Black | 6-3 6-4 | | 0.74 | 3.2% | 0.0% | 46.8% | 69.0% | 39.4% | 8/12 | 1:12 |
| 4‑Oct‑1999 | Shanghai | Hard | R32 | 77 | 97 | Max Mirnyi [BLR] d. Black | 6-3 2-6 6-4 | | 0.94 | 2.7% | 4.1% | 75.3% | 70.9% | 44.4% | 2/5 | 1:24 |
| 27‑Sep‑1999 | Toulouse | Hard | R16 | 79 | 70 | Magnus Gustafsson [SWE] d. Black | 6-4 6-2 | | 0.54 | 1.9% | 1.9% | 74.1% | 65.0% | 28.6% | 3/6 | 1:01 |
| 27‑Sep‑1999 | Toulouse | Hard | R32 | 79 | 68 | Black d. Chris Woodruff [USA] | 6-4 3-6 6-1 | | 1.36 | 16.7% | 2.8% | 72.2% | 71.2% | 75.0% | 3/4 | 1:28 |
| 24‑Sep‑1999 | Davis Cup WG PO: ZIM vs CHI | Hard | RR | 79 | 144 | Black d. Nicolas Massu [CHI] | 4-6 5-7 6-4 6-2 6-3 | | | | | | | | | |
| 24‑Sep‑1999 | Davis Cup WG PO: ZIM vs CHI | Hard | RR | 79 | 8 | Black d. Marcelo Rios [CHI] | 7-6(3) 3-6 6-2 7-6(6) | | | | | | | | | |
| 30‑Aug‑1999 | US Open | Hard | R128 | 67 | 25 | Younes El Aynaoui [MAR] d. Black | 7-6(5) 6-4 6-2 | | 0.74 | 4.4% | 0.0% | 64.8% | 66.1% | 56.3% | 6/10 | 1:51 |
| 16‑Aug‑1999 | Washington | Hard | R64 | 56 | 105 | Martin Damm Sr [CZE] d. (12)Black | 6-2 6-2 | | 0.66 | 2.4% | 9.5% | 45.2% | 52.6% | 39.1% | 0/5 | 0:57 |
| 9‑Aug‑1999 | Cincinnati Masters | Hard | R64 | 56 | 41 | Fabrice Santoro [FRA] d. Black | 7-6(5) 6-3 | | 0.92 | 5.7% | 0.0% | 67.1% | 59.6% | 52.2% | 5/9 | 1:26 |
| 2‑Aug‑1999 | Canada Masters | Hard | R32 | 58 | 243 | (Q)Kevin Ullyett [ZIM] d. Black | 5-7 6-4 7-6(6) | | 1.00 | 6.3% | 5.4% | 57.1% | 67.2% | 50.0% | 3/7 | 2:08 |
| 2‑Aug‑1999 | Canada Masters | Hard | R64 | 58 | 28 | Black d. (13)Goran Ivanisevic [CRO] | 6-4 6-4 | | 1.22 | 2.9% | 1.5% | 64.7% | 63.6% | 62.5% | 6/8 | 1:16 |
| 26‑Jul‑1999 | Los Angeles | Hard | R32 | 55 | 61 | Andrew Ilie [AUS] d. Black | 6-4 7-6(8) | | 0.77 | 6.2% | 3.7% | 53.1% | 62.8% | 50.0% | 8/11 | 1:37 |
| 21‑Jun‑1999 | Wimbledon | Grass | R128 | 47 | 30 | Sebastien Grosjean [FRA] d. Black | 5-7 6-0 7-5 7-5 | | 0.84 | 2.4% | 2.4% | 61.6% | 63.6% | 43.8% | 6/14 | 2:27 |
| 14‑Jun‑1999 | Nottingham | Grass | R32 | 41 | 314 | (WC)Luke Milligan [GBR] d. (6)Black | 6-4 3-6 6-2 | | 0.99 | 9.3% | 7.2% | 53.6% | 73.1% | 35.6% | 10/16 | 1:52 |
| 7‑Jun‑1999 | Queen's Club | Grass | R16 | 37 | 6 | (3)Tim Henman [GBR] d. (13)Black | 6-1 6-4 | | 0.57 | 0.0% | 7.4% | 55.6% | 60.0% | 54.2% | 4/7 | 1:05 |
| 7‑Jun‑1999 | Queen's Club | Grass | R32 | 37 | 75 | (13)Black d. Arnaud Clement [FRA] | 6-4 6-3 | | 1.44 | 5.1% | 3.4% | 50.8% | 66.7% | 62.1% | 4/6 | 1:15 |
| 7‑Jun‑1999 | Queen's Club | Grass | R64 | 37 | 104 | (13)Black d. Roger Federer [SUI] | 6-3 6-0 | | 1.66 | 4.0% | 0.0% | 58.0% | 72.4% | 57.1% | 1/2 | 0:52 |
| 24‑May‑1999 | Roland Garros | Clay | R32 | 39 | 100 | Andrei Medvedev [UKR] d. Black | 6-1 6-2 3-6 6-1 | | 0.67 | 2.9% | 3.8% | 53.8% | 57.1% | 41.7% | 9/17 | 2:05 |
| 24‑May‑1999 | Roland Garros | Clay | R64 | 39 | 91 | Black d. Albert Portas [ESP] | 6-2 6-3 6-2 | | 1.77 | 16.7% | 6.9% | 52.8% | 89.5% | 50.0% | 0/1 | 1:31 |
| 24‑May‑1999 | Roland Garros | Clay | R128 | 39 | 88 | Black d. Adrian Voinea [ROU] | 4-6 3-6 6-3 6-2 6-4 | | 1.03 | 7.8% | 0.6% | 63.6% | 64.3% | 46.4% | 8/15 | 2:55 |
| 12‑Apr‑1999 | Tokyo | Hard | R32 | 24 | 119 | Sebastien Lareau [CAN] d. (6)Black | 6-3 7-5 | | 0.73 | 4.8% | 1.6% | 62.9% | 76.9% | 47.8% | 4/6 | 1:14 |
| 5‑Apr‑1999 | Chennai | Hard | F | 29 | 71 | (4)Black d. (7)Rainer Schuettler [GER] | 6-4 1-6 6-3 | | 1.04 | 6.9% | 4.2% | 59.7% | 69.8% | 48.3% | 1/5 | 1:39 |
| 5‑Apr‑1999 | Chennai | Hard | SF | 29 | 78 | (4)Black d. (8)John Van Lottum [NED] | 6-1 6-1 | | 2.04 | 8.1% | 0.0% | 62.2% | 69.6% | 71.4% | 0/1 | 1:05 |
| 5‑Apr‑1999 | Chennai | Hard | QF | 29 | 83 | (4)Black d. Richard Fromberg [AUS] | 6-4 6-2 | | 1.33 | 1.7% | 0.0% | 63.8% | 70.3% | 76.2% | 1/1 | 1:12 |
| 5‑Apr‑1999 | Chennai | Hard | R16 | 29 | 102 | (4)Black d. Leander Paes [IND] | 6-3 6-2 | | 1.28 | 8.1% | 6.8% | 55.4% | 68.3% | 54.5% | 4/5 | 1:20 |
| 5‑Apr‑1999 | Chennai | Hard | R32 | 29 | 211 | (4)Black d. (Q)Gregory Carraz [FRA] | 6-1 6-3 | | 1.82 | 8.9% | 6.7% | 42.2% | 78.9% | 69.2% | 1/1 | 0:58 |
| 2‑Apr‑1999 | Davis Cup WG R1: ZIM vs AUS | Hard | RR | 29 | 9 | Black d. Mark Philippoussis [AUS] | 6-3 3-6 4-6 6-3 7-5 | | | | | | | | | |
| 2‑Apr‑1999 | Davis Cup WG R1: ZIM vs AUS | Hard | RR | 29 | 5 | Patrick Rafter [AUS] d. Black | 6-4 7-6(2) 6-2 | | | | | | | | | |
| 15‑Mar‑1999 | Miami Masters | Hard | R32 | 28 | 8 | (8)Marcelo Rios [CHI] d. (25)Black | 6-3 6-4 | | 0.86 | 6.3% | 6.3% | 57.8% | 78.4% | 29.6% | 6/9 | 1:15 |
| 15‑Mar‑1999 | Miami Masters | Hard | R64 | 28 | 99 | (25)Black d. (Q)Nicolas Escude [FRA] | 6-4 6-3 | | 1.54 | 6.1% | 4.1% | 40.8% | 75.0% | 65.5% | 1/3 | 1:02 |
| 8‑Mar‑1999 | Indian Wells Masters | Hard | R64 | 28 | 12 | (12)Karol Kucera [SVK] d. Black | 6-4 3-6 6-4 | | 0.99 | 3.6% | 0.0% | 62.7% | 63.5% | 45.2% | 4/10 | 1:54 |
| 1‑Mar‑1999 | Copenhagen | Carpet | SF | 31 | 32 | (3)Magnus Gustafsson [SWE] d. (2)Black | 6-3 6-1 | | 0.47 | 3.8% | 1.9% | 56.6% | 56.7% | 43.5% | 4/8 | 1:03 |
| 1‑Mar‑1999 | Copenhagen | Carpet | QF | 31 | 290 | (2)Black d. (Q)Max Mirnyi [BLR] | 6-7(5) 6-3 6-3 | | 1.38 | 4.5% | 1.1% | 65.2% | 72.4% | 67.7% | 0/1 | 1:59 |
| 1‑Mar‑1999 | Copenhagen | Carpet | R16 | 31 | 320 | (2)Black d. (Q)Nicklas Kulti [SWE] | 7-6(5) 3-6 6-3 | | 1.00 | 4.6% | 3.1% | 63.4% | 63.9% | 47.9% | 15/19 | 2:27 |
| 1‑Mar‑1999 | Copenhagen | Carpet | R32 | 31 | 867 | (2)Black d. (WC)Kristian Pless [DEN] | 6-2 6-3 | | 1.58 | 5.3% | 3.5% | 61.4% | 68.6% | 68.2% | 7/8 | 1:08 |
| 22‑Feb‑1999 | London | Carpet | R16 | 31 | 2 | (1)Yevgeny Kafelnikov [RUS] d. Black | 6-3 6-2 | | 0.62 | 1.8% | 3.6% | 64.3% | 58.3% | 45.0% | 2/5 | 1:03 |
| 22‑Feb‑1999 | London | Carpet | R32 | 31 | 66 | Black d. Karim Alami [MAR] | 6-1 1-6 7-6(4) | | 1.07 | 5.8% | 3.5% | 57.0% | 65.3% | 59.5% | 4/6 | 1:50 |
| 15‑Feb‑1999 | Rotterdam | Carpet | R32 | 31 | 11 | (6)Karol Kucera [SVK] d. Black | 6-1 6-1 | | 0.50 | 0.0% | 0.0% | 62.3% | 48.5% | 40.0% | 9/14 | 0:58 |
| 8‑Feb‑1999 | Dubai | Hard | R16 | 32 | | (7)Felix Mantilla [ESP] d. Black | 7-6(1) 6-3 | | 0.73 | 8.9% | 2.5% | 63.3% | 70.0% | 31.0% | 6/9 | 1:39 |
| 8‑Feb‑1999 | Dubai | Hard | R32 | 32 | 31 | Black d. Bohdan Ulihrach [CZE] | 6-1 7-6(7) | | 1.72 | 10.8% | 0.0% | 53.8% | 77.1% | 73.3% | 1/1 | 1:23 |
| 18‑Jan‑1999 | Australian Open | Hard | R64 | 28 | 21 | Thomas Enqvist [SWE] d. Black | 7-6(6) 7-6(2) 6-0 | | 0.58 | 5.3% | 1.8% | 69.3% | 69.6% | 31.4% | 3/7 | 2:00 |
| 18‑Jan‑1999 | Australian Open | Hard | R128 | 28 | 248 | Black d. (WC)Toby Mitchell [AUS] | 7-6 6-2 6-2 | | 1.55 | 5.4% | 4.3% | 71.0% | 81.8% | 37.0% | 6/7 | 1:45 |
| 11‑Jan‑1999 | Auckland | Hard | R32 | 27 | 55 | Guillaume Raoux [FRA] d. (4)Black | 6-3 6-3 | | 0.57 | 3.0% | 1.5% | 59.1% | 59.0% | 40.7% | 5/9 | 1:17 |
| 4‑Jan‑1999 | Adelaide | Hard | QF | 28 | 27 | (4)Jason Stoltenberg [AUS] d. (5)Black | 6-3 6-2 | | 0.48 | 1.6% | 4.8% | 58.1% | 44.4% | 53.8% | 6/10 | 1:05 |
| 4‑Jan‑1999 | Adelaide | Hard | R16 | 28 | 68 | (5)Black d. Andrei Pavel [ROU] | 6-3 6-2 | | 1.40 | 6.2% | 0.0% | 61.5% | 67.5% | 68.0% | 3/3 | 1:20 |
| 4‑Jan‑1999 | Adelaide | Hard | R32 | 28 | 42 | (5)Black d. Vincent Spadea [USA] | 1-6 7-6(6) 6-2 | | 1.18 | 6.3% | 5.1% | 57.0% | 77.8% | 52.9% | 3/6 | 2:00 |