| Year | Tournament | Result | Player | Age | Nation |
|---|---|---|---|---|---|
| 1999 | US Open | R128 | Tatiana Poutchek | 20 | Belarus |
| 1999 | US Open | R128 | Wang Shi-ting | 25 | Taiwan |
| 1999 | US Open | R128 | Meghann Shaughnessy | 20 | United States |
| 1999 | US Open | R128 | Jill Craybas | 25 | United States |
| 1999 | US Open | R128 | Silvija Talaja | 21 | Croatia |
| 1999 | US Open | R128 | Erika deLone | 26 | United States |
| 1999 | US Open | R128 | Miriam Oremans | 26 | Netherlands |
| 1999 | US Open | R128 | Kristina Brandi | 22 | Puerto Rico |
| 1999 | US Open | R128 | Justine Henin | 17 | Belgium |
| 1999 | US Open | R128 | Jelena Dokic | 16 | Australia |
| 1999 | US Open | R128 | Meilen Tu | 21 | United States |
| 1999 | US Open | R128 | Émilie Loit | 20 | France |
| 1999 | US Open | R128 | Cristina Torrens-Valero | 24 | Spain |
| 1999 | US Open | R128 | Sandra Kleinová | 21 | Czech Republic |
| 1999 | US Open | R128 | Zuzana Lesenarova | 22 | Czech Republic |
| 1999 | US Open | R128 | Lisa McShea | 24 | Australia |
| 1999 | US Open | R128 | Barbara Schwartz | 20 | Austria |
| 1999 | US Open | R128 | Janet Lee | 22 | Taiwan |
| 1999 | US Open | R128 | Jennifer Hopkins | 18 | United States |
| 1999 | US Open | R128 | Alexandra Stevenson | 18 | United States |
| 1999 | US Open | R128 | Chanda Rubin | 23 | United States |
| 1999 | US Open | R128 | Katarina Srebotnik | 18 | Slovenia |
| 1999 | US Open | R128 | Christína Papadáki | 26 | Greece |
| 1999 | US Open | R128 | Laura Granville | 18 | United States |
| 1999 | US Open | R128 | Anca Barna | 22 | Germany |
| 1999 | US Open | R128 | Nathalie Dechy | 20 | France |
| 1999 | US Open | R128 | Mashona Washington | 23 | United States |
| 1999 | US Open | R128 | Květa Peschke | 24 | Czech Republic |
| 1999 | US Open | R128 | Maureen Drake | 28 | Canada |
| 1999 | US Open | R128 | Amanda Coetzer | 27 | South Africa |
| 1999 | US Open | R128 | Tatiana Panova | 23 | Russia |
| 1999 | US Open | R128 | Denisa Chládková | 20 | Czech Republic |
| 1999 | US Open | R128 | Cătălina Cristea | 24 | Romania |
| 1999 | US Open | R128 | Emmanuelle Gagliardi | 23 | Switzerland |
| 1999 | US Open | R128 | Elena Pampoulova | 27 | Germany |
| 1999 | US Open | R128 | Andrea Glass | 23 | Germany |
| 1999 | US Open | R128 | Tracy Almeda | 19 | United States |
| 1999 | US Open | R128 | Corina Morariu | 21 | United States |
| 1999 | Wimbledon | W | Pete Sampras | 27 | United States |
| 1999 | Wimbledon | W | Lindsay Davenport | 23 | United States |
| 1999 | Wimbledon | F | Andre Agassi | 29 | United States |
| 1999 | Wimbledon | F | Steffi Graf | 30 | Germany |
| 1999 | Wimbledon | S | Tim Henman | 24 | United Kingdom |
| 1999 | Wimbledon | S | Pat Rafter | 26 | Australia |
| 1999 | Wimbledon | S | Alexandra Stevenson | 18 | United States |
| 1999 | Wimbledon | S | Mirjana Lučić-Baroni | 17 | Croatia |
| 1999 | Wimbledon | Q | Todd Martin | 28 | United States |
| 1999 | Wimbledon | Q | Mark Philippoussis | 22 | Australia |
| 1999 | Wimbledon | Q | Gustavo Kuerten | 22 | Brazil |
| 1999 | Wimbledon | Q | Cédric Pioline | 30 | France |
Open Era Grand Slam Tennis