Moscow, Russia; 08.11.1999; WS; Indoor: Carpet; Draw: 32 ; Partner: Kitinov, Aleksandar (MKD)
| Round | Opponent | Ranking | Score | |
| R16 | David Adams (RSA) / John-Laffnie de Jager (RSA) | 13 / 18 | L 6-7(0), 6-3, 4-6 |
This Event Points: 1, South African Airways ATP Ranking: 87, Prize Money: $750
Brest, France; 25.10.1999; CH; Indoor: Hard; Draw: 32 ; Partner: Waite, Jack (USA)
| Round | Opponent | Ranking | Score | |
| R16 | Juan Ignacio Carrasco (ESP) / Jairo Velasco Jr (ESP) | 103 / 103 | W 7-5, 6-3 | |
| Q | Petr Pala (CZE) / Pavel Vizner (CZE) | 97 / 81 | W 6-3, 6-7(4), 7-6(8) | |
| S | Rodolphe Gilbert (FRA) / Lionel Roux (FRA) | 467 / 403 | L 4-6, 5-7 |
This Event Points: 36, South African Airways ATP Ranking: 96, Prize Money: $1,070
Eckental, Germany; 18.10.1999; CH; Indoor: Carpet; Draw: 32 ; Partner: Luxa, Petr (CZE)
| Round | Opponent | Ranking | Score | |
| R16 | Marcus Hilpert (GER) / Robert Lindstedt (SWE) | 167 / 326 | W 7-6(1), 6-7(7), 7-5 | |
| Q | Petr Pala (CZE) / Pavel Vizner (CZE) | 102 / 65 | L 4-6, 6-3, 5-7 |
This Event Points: 10, South African Airways ATP Ranking: 96, Prize Money: $160
Bucharest, Romania; 27.09.1999; WS; Outdoor: Clay; Draw: 32 ; Partner: Vemic, Dusan (SRB)
| Round | Opponent | Ranking | Score | |
| R16 | Marc-Kevin Goellner (GER) / Francisco Montana (USA) | 99 / 71 | L 3-6, 7-6(6), 5-7 |
This Event Points: 10, South African Airways ATP Ranking: 93, Prize Money: $750
Tashkent, Uzbekistan; 13.09.1999; WS; Outdoor: Hard; Draw: 32 ; Partner: Wessels, Peter (NED)
| Round | Opponent | Ranking | Score | |
| R16 | Roger Federer (SUI) / Sander Groen (NED) | 181 / 141 | L 6-3, 5-7, 3-6 |
This Event Points: 1, South African Airways ATP Ranking: 90, Prize Money: $750
US Open, NY, U.S.A.; 30.08.1999; GS; Outdoor: Hard; Draw: 128 ; Partner: MacPhie, Brian (USA)
| Round | Opponent | Ranking | Score | |
| R64 | Goran Ivanisevic (CRO) / Jeff Tarango (USA) | 41 / 17 | W 6-4, 2-6, 6-1 | |
| R32 | Andrew Florent (AUS) / David Macpherson (AUS) | 29 / 44 | W 7-6(3), 6-3 | |
| R16 | Andrei Olhovskiy (RUS) / David Prinosil (GER) | 48 / 52 | L 6-7(3), 3-6 |
This Event Points: 115, South African Airways ATP Ranking: 91, Prize Money: $11,250
Washington, DC, U.S.A.; 16.08.1999; CS; Outdoor: Hard; Draw: 56 ; Partner: Kiefer, Nicolas (GER)
| Round | Opponent | Ranking | Score | |
| R32 | Martin Damm (CZE) / Laurence Tieleman (ITA) | 56 / 119 | W 6-3, 6-4 | |
| R16 | Piet Norval (RSA) / Kevin Ullyett (ZIM) | 37 / 36 | L 3-6, 4-6 |
This Event Points: 22, South African Airways ATP Ranking: 89, Prize Money: $1,450
Newport, RI, U.S.A.; 05.07.1999; WS; Outdoor: Grass; Draw: 32 ; Partner: Ferreira, Wayne (RSA)
| Round | Opponent | Ranking | Score | |
| R16 | Max Mirnyi (BLR) / Sandon Stolle (AUS) | 50 / 3 | W 6-4, 7-6(4) | |
| Q | David Dilucia (USA) / Laurence Tieleman (ITA) | 108 / 141 | L W/O |
This Event Points: 38, South African Airways ATP Ranking: 89, Prize Money: $1,700
Wimbledon, England; 21.06.1999; GS; Outdoor: Grass; Draw: 128 ; Partner: Djordjevic, Nebojsa (SCG)
| Round | Opponent | Ranking | Score | |
| R64 | Piet Norval (RSA) / Kevin Ullyett (ZIM) | 32 / 33 | L 6-4, 1-6, 3-6, 6-3, 8-10 |
This Event Points: 1, South African Airways ATP Ranking: 90, Prize Money: $3,350
London / Queen’s Club, England; 07.06.1999; WS; Outdoor: Grass; Draw: 56 ; Partner: Greenhalgh, James (NZL)
| Round | Opponent | Ranking | Score | |
| R32 | Wayne Arthurs (AUS) / Andrew Kratzmann (AUS) | 26 / 37 | L 3-6, 4-6 |
This Event Points: 1, South African Airways ATP Ranking: 80, Prize Money: $750
Birmingham, AL, U.S.A.; 10.05.1999; CH; Outdoor: Clay; Draw: 32 ; Partner: Seguso, Robert (USA)
| Round | Opponent | Ranking | Score | |
| R16 | Maurice Ruah (VEN) / Byron Talbot (RSA) | 154 / 131 | W 7-6, 3-6, 6-3 | |
| Q | David Roditi (MEX) / Jack Waite (USA) | 70 / 78 | L 3-6, 6-7 |
This Event Points: 14, South African Airways ATP Ranking: 82, Prize Money: $315
Delray Beach, FL, U.S.A.; 03.05.1999; WS; Outdoor: Clay; Draw: 32 ; Partner: Mirnyi, Max (BLR)
| Round | Opponent | Ranking | Score | |
| R16 | Lucas Arnold Ker (ARG) / Mariano Hood (ARG) | 79 / 74 | W 6-1, 7-6 | |
| Q | Diego Del Rio (ARG) / Jaime Oncins (BRA) | 82 / 100 | W 6-3, 6-1 | |
| S | Alberto Martin (ESP) / Paul Rosner (RSA) | 89 / 97 | W 7-5, 6-3 | |
| W | Doug Flach (USA) / Brian MacPhie (USA) | 99 / 77 | W 7-6(3), 3-6, 6-3 |
This Event Points: 122, South African Airways ATP Ranking: 92, Prize Money: $8,200
Orlando, FL, U.S.A.; 19.04.1999; WS; Outdoor: Clay; Draw: 32 ; Partner: Grabb, Jim (USA)
| Round | Opponent | Ranking | Score | |
| R16 | Jan-Michael Gambill (USA) / Alex O’Brien (USA) | 205 / 25 | W 6-3, 5-7, 6-4 | |
| Q | Lucas Arnold Ker (ARG) / Mariano Hood (ARG) | 82 / 71 | L 4-6, 5-7 |
This Event Points: 26, South African Airways ATP Ranking: 92, Prize Money: $1,450
ATP Masters Series Miami, FL, U.S.A; 15.03.1999; SU; Outdoor: Hard; Draw: 96 ; Partner: Kitinov, Aleksandar (MKD)
| Round | Opponent | Ranking | Score | |
| R64 | Tomas Carbonell (ESP) / Donald Johnson (USA) | 52 / 33 | L 6-2, 3-6, 4-6 |
This Event Points: 1, South African Airways ATP Ranking: 84, Prize Money: $1,500
Salinas, Ecuador; 08.03.1999; CH; Outdoor: Hard; Draw: 32 ; Partner: Vemic, Dusan (SRB)
| Round | Opponent | Ranking | Score | |
| R16 | Lan Bale (RSA) / Michael Tebbutt (AUS) | 72 / 84 | L 6-3, 4-6, 3-6 |
This Event Points: 1, South African Airways ATP Ranking: 87, Prize Money: $275
Scottsdale, AZ, U.S.A.; 01.03.1999; WS; Outdoor: Hard; Draw: 32 ; Partner: Palmer, Jared (USA)
| Round | Opponent | Ranking | Score | |
| R16 | Paul Kilderry (AUS) / Xavier Malisse (BEL) | 107 / 442 | W 6-3, 6-1 | |
| Q | Chris Haggard (RSA) / Aleksandar Kitinov (MKD) | 43 / 84 | W 7-6, 6-2 | |
| S | Justin Gimelstob (USA) / Richey Reneberg (USA) | 52 / 37 | L 3-6, 3-6 |
This Event Points: 73, South African Airways ATP Ranking: 97, Prize Money: $3,935
San Jose, CA, U.S.A.; 08.02.1999; WS; Indoor: Hard; Draw: 32 ; Partner: Kitinov, Aleksandar (MKD)
| Round | Opponent | Ranking | Score | |
| R16 | Justin Gimelstob (USA) / Brian MacPhie (USA) | 52 / 84 | W 6-4, 4-6, 7-6 | |
| Q | Jim Grabb (USA) / Richey Reneberg (USA) | 18 / 28 | W 4-6, 6-1, 6-4 | |
| S | Alex O’Brien (USA) / Jared Palmer (USA) | 19 / 61 | W 6-3, 6-7, 7-5 | |
| F | Todd Woodbridge (AUS) / Mark Woodforde (AUS) | 8 / 8 | L 5-7, 7-6(3), 4-6 |
This Event Points: 125, South African Airways ATP Ranking: 118, Prize Money: $6,645
Australian Open, Australia; 18.01.1999; GS; Outdoor: Hard; Draw: 128 ; Partner: Pescariu, Dinu (ROU)
| Round | Opponent | Ranking | Score | |
| R64 | Todd Woodbridge (AUS) / Mark Woodforde (AUS) | 6 / 6 | L 6-3, 3-6, 7-9 |
This Event Points: 1, South African Airways ATP Ranking: 123, Prize Money: $2,034
