| 11‑Aug‑2003 | Cincinnati Masters | Hard | R64 | 114 | 2 | (3)Roger Federer [SUI] d. (Q)Draper | 4-6 6-3 7-6(10) | | 0.81 | 5.7% | 0.9% | 61.3% | 73.8% | 58.5% | 7/8 | 2:02 |
| 10‑Aug‑1998 | Cincinnati Masters | Hard | R16 | 46 | 10 | (7)Yevgeny Kafelnikov [RUS] d. Draper | 6-3 6-3 | | 0.47 | 12.9% | 2.9% | 52.9% | 73.0% | 42.4% | 6/9 | 1:03 |
| 10‑Aug‑1998 | Cincinnati Masters | Hard | R32 | 46 | 12 | Draper d. (9)Alex Corretja [ESP] | 6-3 6-7(5) 7-6(5) | | 1.13 | 10.3% | 1.7% | 62.1% | 75.0% | 56.8% | 6/8 | 2:28 |
| 10‑Aug‑1998 | Cincinnati Masters | Hard | R64 | 46 | 56 | Draper d. Nicolas Lapentti [ECU] | 6-4 4-6 7-5 | | 1.17 | 4.6% | 3.4% | 65.5% | 77.2% | 53.3% | 4/6 | 1:56 |
| 4‑Aug‑1997 | Cincinnati Masters | Hard | R32 | 69 | 8 | (6)Sergi Bruguera [ESP] d. Draper | 7-6(6) 6-2 | | 0.82 | 9.5% | 0.0% | 58.1% | 58.1% | 61.3% | 5/8 | 1:29 |
| 4‑Aug‑1997 | Cincinnati Masters | Hard | R64 | 69 | 58 | Draper d. Richey Reneberg [USA] | 1-6 7-6(3) 6-4 | | 1.11 | 11.1% | 1.1% | 61.1% | 76.4% | 57.1% | 1/3 | 1:51 |
| 5‑Aug‑1996 | Cincinnati Masters | Hard | R64 | 83 | 456 | (Q)Sasa Hirszon [CRO] d. (Q)Draper | 6-1 RET | | 0.31 | 3.2% | 0.0% | 41.9% | 46.2% | 33.3% | 6/9 | 0:31 |