| Year | Tournament | Result | Player | Age | Nation |
|---|---|---|---|---|---|
| 1999 | Wimbledon | R64 | Ruxandra Dragomir | 26 | Romania |
| 1999 | Wimbledon | R64 | Katarína Studeníková | 26 | Slovakia |
| 1999 | Wimbledon | R64 | Louise Latimer | 21 | United Kingdom |
| 1999 | Wimbledon | R64 | Sabine Appelmans | 27 | Belgium |
| 1999 | Wimbledon | R64 | Meghann Shaughnessy | 20 | United States |
| 1999 | Wimbledon | R64 | Olga Barabanschikova | 19 | Belarus |
| 1999 | Wimbledon | R64 | Tara Snyder | 22 | United States |
| 1999 | Wimbledon | R64 | Arantxa Sánchez Vicario | 27 | Spain |
| 1999 | Wimbledon | R64 | Brie Rippner | 19 | United States |
| 1999 | Wimbledon | R64 | Rita Grande | 24 | Italy |
| 1999 | Wimbledon | R64 | Natasha Zvereva | 28 | Belarus |
| 1999 | Wimbledon | R64 | Alexia Dechaume-Balleret | 29 | France |
| 1999 | Wimbledon | R64 | Silvia Farina Elia | 27 | Italy |
| 1999 | Wimbledon | R64 | Karina Habšudová | 25 | Slovakia |
| 1999 | Wimbledon | R64 | Nicole Arendt | 29 | United States |
| 1999 | Wimbledon | R64 | Amélie Cocheteux | 21 | France |
| 1999 | Wimbledon | R128 | Julian Alonso-Pintor | 21 | Spain |
| 1999 | Wimbledon | R128 | Hernán Gumy | 27 | Argentina |
| 1999 | Wimbledon | R128 | Bernd Karbacher | 31 | Germany |
| 1999 | Wimbledon | R128 | Peter Wessels | 21 | Netherlands |
| 1999 | Wimbledon | R128 | Nuno Marques | 29 | Portugal |
| 1999 | Wimbledon | R128 | Magnus Gustafsson | 32 | Sweden |
| 1999 | Wimbledon | R128 | Adrian Voinea | 24 | Romania |
| 1999 | Wimbledon | R128 | Grant Stafford | 28 | South Africa |
| 1999 | Wimbledon | R128 | Hendrik Dreekmann | 24 | Germany |
| 1999 | Wimbledon | R128 | Laurence Tieleman | 26 | Italy |
| 1999 | Wimbledon | R128 | Roger Federer | 17 | Switzerland |
| 1999 | Wimbledon | R128 | Stefan Koubek | 22 | Austria |
| 1999 | Wimbledon | R128 | Justin Gimelstob | 22 | United States |
| 1999 | Wimbledon | R128 | Marcelo Filippini | 31 | Uruguay |
| 1999 | Wimbledon | R128 | Markus Hipfl | 21 | Austria |
| 1999 | Wimbledon | R128 | Takao Suzuki | 22 | Japan |
| 1999 | Wimbledon | R128 | Hicham Arazi | 25 | Morocco |
| 1999 | Wimbledon | R128 | Wayne Black | 25 | Zimbabwe |
| 1999 | Wimbledon | R128 | Cecil Mamiit | 22 | Philippines |
| 1999 | Wimbledon | R128 | Miles Maclagan | 24 | United Kingdom |
| 1999 | Wimbledon | R128 | John van Lottum | 23 | Netherlands |
| 1999 | Wimbledon | R128 | Christian Vinck | 23 | Germany |
| 1999 | Wimbledon | R128 | Mikael Tillström | 27 | Sweden |
| 1999 | Wimbledon | R128 | Richey Reneberg | 33 | United States |
| 1999 | Wimbledon | R128 | Martin Rodriguez | 29 | Argentina |
| 1999 | Wimbledon | R128 | Vincenzo Santopadre | 27 | Italy |
| 1999 | Wimbledon | R128 | Vladimir Voltchkov | 21 | Belarus |
| 1999 | Wimbledon | R128 | Davide Sanguinetti | 26 | Italy |
| 1999 | Wimbledon | R128 | Barry Cowan | 24 | United Kingdom |
| 1999 | Wimbledon | R128 | Gastón Gaudio | 20 | Argentina |
| 1999 | Wimbledon | R128 | Ján Krošlák | 24 | Slovakia |
| 1999 | Wimbledon | R128 | Alejandro Hernandez | 21 | Mexico |
| 1999 | Wimbledon | R128 | Leander Paes | 26 | India |
| 1999 | Wimbledon | R128 | Luke Milligan | 22 | United Kingdom |
Open Era Grand Slam Tennis