Matches — 1999
W-L: 3-7 (30.00%)
| Date | Tournament | Surface | Round | Wrk | Winner | Lrk | Loser | Score |
|---|---|---|---|---|---|---|---|---|
| 1999-08-02 | Canada Masters | Hard | R32 | 2 | 157 | 6-0 6-2 | ||
| 1999-08-02 | Canada Masters | Hard | R64 | 157 | 82 | 7-5 4-6 6-3 | ||
| 1999-07-26 | Los Angeles | Hard | R32 | 33 | 156 | 6-3 6-2 | ||
| 1999-07-16 | Davis Cup WG QF: USA vs AUS | Hard | RR | 32 | 185 | 7-5 6-4 | ||
| 1999-04-19 | Orlando | Clay | R32 | 88 | 176 | 7-5 6-3 | ||
| 1999-03-15 | Miami Masters | Hard | R64 | 29 | 181 | 7-5 7-5 | ||
| 1999-03-15 | Miami Masters | Hard | R128 | 181 | 105 | 7-5 7-6(7) | ||
| 1999-03-01 | Scottsdale | Hard | R32 | 5 | 178 | 6-3 6-4 | ||
| 1999-02-15 | Memphis | Hard | R64 | 185 | 172 | 6-4 6-2 | ||
| 1999-02-15 | Memphis | Hard | R32 | 22 | 185 | 6-4 6-4 |
Alex O'Brien
W-L: 3-7 (30.00%)