| 1999-09-24 | Davis Cup WG PO: NZL vs ESP | Hard | RR | 32 |  Francisco Clavet | 185 |  Brett Steven | 6-2 6-4 6-4 | H2H | 5 | - | - | - | - | - | - | - |
| 1999-04-12 | Tokyo | Hard | R64 | 101 |  Jens Knippschild | 123 | Brett Steven | 6-2 7-5 | H2H | 3 | 73 | 4 | 2 | 50.0% | 88.0% | 68.0% | 0/1 |
| 1999-04-05 | Hong Kong | Hard | R16 | 117 | Bernd Karbacher | 133 | Brett Steven | 6-4 6-0 | H2H | 3 | 60 | 9 | 2 | 65.2% | 73.3% | 62.5% | 0/1 |
| 1999-04-05 | Hong Kong | Hard | R32 | 133 | Brett Steven | 204 |  Steve Campbell | 6-4 6-1 | H2H | 3 | 73 | 3 | 3 | 68.4% | 69.2% | 55.6% | 3/5 |
| 1999-04-02 | Davis Cup G1 SF: NZL vs KOR | Hard | RR | 132 | Brett Steven | 1069 |  Hyeong-Keun Song | 6-3 6-4 6-4 | H2H | 5 | - | - | - | - | - | - | - |
| 1999-02-15 | Memphis | Hard | R64 | 303 | Jonathan Stark (Q) | 103 | Brett Steven | 6-2 6-3 | H2H | 3 | 62 | 13 | 2 | 66.7% | 80.0% | 60.0% | 0/0 |
| 1999-02-08 | San Jose | Hard | R32 | 57 |  Ramon Delgado (8) | 92 | Brett Steven | 5-7 6-4 7-5 | H2H | 3 | 116 | 7 | 3 | 53.0% | 67.9% | 51.1% | 3/7 |
| 1999-01-18 | Australian Open | Hard | R128 | 27 | Michael Chang | 90 | Brett Steven | 7-6(7) 6-3 6-3 | H2H | 5 | 125 | 5 | 2 | 49.5% | 83.3% | 51.0% | 1/3 |
| 1999-01-11 | Auckland | Hard | SF | 74 |  Sjeng Schalken | 100 | Brett Steven (WC) | 6-4 6-4 | H2H | 3 | 70 | 3 | 0 | 69.4% | 82.4% | 86.7% | 0/0 |
| 1999-01-11 | Auckland | Hard | QF | 100 | Brett Steven (WC) | 59 |  Mariano Zabaleta | 6-0 6-4 | H2H | 3 | 56 | 5 | 1 | 75.5% | 70.3% | 50.0% | 5/6 |
