| 31‑Aug‑1998 | US Open | Hard | R128 | 46 | 13 | (13)Tim Henman [GBR] d. Draper | 6-3 7-6(4) 7-6(3) | | 0.78 | 4.5% | 1.8% | 58.0% | 72.3% | 59.6% | 6/8 | |
| 17‑Aug‑1998 | Indianapolis | Hard | R32 | 45 | 11 | (6)Alex Corretja [ESP] d. Draper | 6-3 6-7(2) 7-5 | | 0.83 | 7.5% | 0.0% | 65.8% | 64.6% | 56.1% | 7/10 | 2:30 |
| 17‑Aug‑1998 | Indianapolis | Hard | R64 | 45 | 116 | Draper d. (Q)Laurence Tieleman [ITA] | 6-4 6-7(5) 6-3 | | 1.59 | 6.0% | 1.2% | 53.0% | 75.0% | 74.4% | 1/3 | 1:58 |
| 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 |
| 3‑Aug‑1998 | Canada Masters | Hard | R32 | 46 | 7 | (5)Jonas Bjorkman [SWE] d. Draper | 7-6(5) 6-3 | | 0.85 | 5.6% | 2.8% | 46.5% | 75.8% | 47.4% | 3/5 | 1:31 |
| 3‑Aug‑1998 | Canada Masters | Hard | R64 | 46 | 71 | Draper d. Jim Courier [USA] | 7-5 5-7 6-4 | | 1.04 | 9.8% | 3.9% | 52.9% | 79.6% | 56.3% | 5/7 | 2:14 |
| 20‑Jul‑1998 | Washington | Hard | F | 71 | 18 | (2)Andre Agassi [USA] d. (14)Draper | 6-2 6-0 | | 0.41 | 10.5% | 0.0% | 39.5% | 60.0% | 21.7% | 5/10 | 0:50 |
| 20‑Jul‑1998 | Washington | Hard | SF | 71 | 19 | (14)Draper d. (1)Michael Chang [USA] | W/O | | | | | | | | | |
| 20‑Jul‑1998 | Washington | Hard | QF | 71 | 44 | (14)Draper d. (5)Filip Dewulf [BEL] | 6-3 6-2 | | 2.20 | 20.0% | 2.2% | 64.4% | 86.2% | 68.8% | 0/0 | 0:50 |
| 20‑Jul‑1998 | Washington | Hard | R16 | 71 | 31 | (14)Draper d. (4)Byron Black [ZIM] | 6-4 6-2 | | 1.64 | 16.0% | 0.0% | 62.0% | 80.6% | 57.9% | 3/4 | 1:02 |
| 20‑Jul‑1998 | Washington | Hard | R32 | 71 | 92 | (14)Draper d. Wayne Black [ZIM] | 4-6 6-3 7-6(6) | | 1.00 | 13.6% | 2.7% | 52.7% | 74.1% | 48.1% | 9/12 | 2:17 |
| 20‑Jul‑1998 | Washington | Hard | R64 | 71 | 169 | (14)Draper d. Alejandro Hernandez [MEX] | 6-3 3-6 6-4 | | 1.10 | 7.5% | 1.3% | 58.8% | 74.5% | 63.6% | 0/1 | 1:39 |
| 6‑Jul‑1998 | Newport | Grass | R16 | 68 | 120 | Leander Paes [IND] d. (6)Draper | 7-5 6-4 | | 0.80 | 4.2% | 4.2% | 52.8% | 71.1% | 50.0% | 3/6 | 1:10 |
| 6‑Jul‑1998 | Newport | Grass | R32 | 68 | 149 | (6)Draper d. Oscar Burrieza [ESP] | 6-3 7-5 | | 1.49 | 14.5% | 6.5% | 64.5% | 85.0% | 50.0% | 4/5 | 1:08 |
| 22‑Jun‑1998 | Wimbledon | Grass | R64 | 69 | 17 | Thomas Enqvist [SWE] d. Draper | 6-7(5) 6-1 6-4 6-3 | | 0.74 | 10.3% | 4.8% | 56.2% | 81.7% | 39.1% | 11/17 | 2:15 |
| 22‑Jun‑1998 | Wimbledon | Grass | R128 | 69 | 114 | Draper d. Rainer Schuettler [GER] | 6-3 7-5 3-6 6-3 | | 1.21 | 0.8% | 3.4% | 52.9% | 73.0% | 51.8% | 4/8 | 2:06 |
| 15‑Jun‑1998 | Nottingham | Grass | QF | 73 | 93 | Jerome Golmard [FRA] d. Draper | 6-4 6-3 | | 0.49 | 12.7% | 3.6% | 56.4% | 67.7% | 50.0% | 3/6 | 0:59 |
| 15‑Jun‑1998 | Nottingham | Grass | R16 | 73 | 10 | Draper d. (4)Cedric Pioline [FRA] | 6-3 1-1 DEF | | 1.72 | 12.1% | 6.1% | 54.5% | 88.9% | 60.0% | 0/0 | 0:50 |
| 15‑Jun‑1998 | Nottingham | Grass | R32 | 73 | 111 | Draper d. (Q)Justin Gimelstob [USA] | 6-3 4-6 7-6(4) | | 1.00 | 4.2% | 0.0% | 54.2% | 63.1% | 56.4% | 10/14 | 2:16 |
| 8‑Jun‑1998 | Queen's Club | Grass | F | 108 | 253 | Draper d. (Q)Laurence Tieleman [ITA] | 7-6(5) 6-4 | | 1.19 | 14.9% | 1.5% | 55.2% | 83.8% | 66.7% | 0/0 | 1:12 |
| 8‑Jun‑1998 | Queen's Club | Grass | SF | 108 | 66 | Draper d. (15)Mark Woodforde [AUS] | 6-3 6-2 | | 1.42 | 4.1% | 4.1% | 53.1% | 80.8% | 43.5% | 1/2 | 1:00 |
| 8‑Jun‑1998 | Queen's Club | Grass | QF | 108 | 222 | Draper d. (Q)Doug Flach [USA] | 7-6(7) 7-6(5) | | 1.14 | 10.8% | 2.4% | 44.6% | 78.4% | 52.2% | 2/6 | 1:35 |
| 8‑Jun‑1998 | Queen's Club | Grass | R16 | 108 | 43 | Draper d. (13)Brett Steven [NZL] | 7-6(6) 7-6(3) | | 1.09 | 4.9% | 4.9% | 48.1% | 74.4% | 59.5% | 0/2 | 1:32 |
| 8‑Jun‑1998 | Queen's Club | Grass | R32 | 108 | 6 | Draper d. (3)Patrick Rafter [AUS] | 4-6 7-5 6-4 | | 1.01 | 4.5% | 8.2% | 50.0% | 78.2% | 49.1% | 7/9 | 2:00 |
| 8‑Jun‑1998 | Queen's Club | Grass | R64 | 108 | 106 | Draper d. Michael Tebbutt [AUS] | 6-4 2-6 6-4 | | 1.00 | 1.9% | 13.1% | 48.6% | 69.2% | 40.0% | 6/11 | |
| 25‑May‑1998 | Roland Garros | Clay | R64 | 121 | 148 | 6-3 3-6 6-7(5) 7-6(2) 6-2 | | 1.04 | 6.1% | 0.6% | 64.4% | 71.6% | 45.3% | 11/18 | 3:13 |
| 25‑May‑1998 | Roland Garros | Clay | R128 | 121 | 81 | Draper d. Tomas Nydahl [SWE] | 6-3 7-6(2) 6-3 | | 1.24 | 5.6% | 4.0% | 50.8% | 76.2% | 49.2% | 5/8 | 2:00 |
| 18‑May‑1998 | St. Poelten | Clay | R32 | 120 | 3 | (1)Marcelo Rios [CHI] d. Draper | 6-1 6-3 | | 0.43 | 3.6% | 5.4% | 64.3% | 55.6% | 40.0% | 7/11 | 0:50 |
| 20‑Apr‑1998 | Orlando | Clay | R32 | 81 | 68 | Andrei Pavel [ROU] d. Draper | 7-5 6-0 | | 0.60 | 1.9% | 3.8% | 69.2% | 50.0% | 31.3% | 3/8 | 0:57 |
| 16‑Mar‑1998 | Miami Masters | Hard | R128 | 72 | 128 | (Q)Dennis Van Scheppingen [NED] d. Draper | 6-7(3) 7-5 6-3 | | 0.93 | 5.8% | 0.8% | 57.5% | 65.2% | 52.9% | 5/9 | 2:14 |
| 9‑Mar‑1998 | Indian Wells Masters | Hard | R32 | 77 | 2 | (2)Petr Korda [CZE] d. (Q)Draper | 6-3 3-6 6-0 | | 0.69 | 3.9% | 1.3% | 59.2% | 51.1% | 54.8% | 8/13 | 1:22 |
| 9‑Mar‑1998 | Indian Wells Masters | Hard | R64 | 77 | 58 | (Q)Draper d. (Q)Andrea Gaudenzi [ITA] | 6-4 4-6 6-4 | | 1.11 | 5.5% | 1.8% | 58.2% | 68.8% | 37.0% | 11/16 | 1:56 |
| 2‑Mar‑1998 | Scottsdale | Hard | R32 | 80 | 28 | (4)Nicolas Kiefer [GER] d. (LL)Draper | 6-3 6-4 | | 0.63 | 9.1% | 3.6% | 54.5% | 70.0% | 52.0% | 4/6 | 1:05 |
| 19‑Jan‑1998 | Australian Open | Hard | R64 | 76 | 7 | (6)Petr Korda [CZE] d. Draper | 7-6(3) 6-3 6-3 | | 0.80 | 8.7% | 2.9% | 61.5% | 70.3% | 52.5% | 1/5 | 1:45 |
| 19‑Jan‑1998 | Australian Open | Hard | R128 | 76 | 37 | Draper d. Dominik Hrbaty [SVK] | 6-4 7-5 7-5 | | 1.39 | 7.3% | 1.8% | 51.8% | 77.2% | 58.5% | 4/7 | 2:00 |
| 12‑Jan‑1998 | Sydney Outdoor | Hard | R16 | 77 | 27 | Thomas Enqvist [SWE] d. (WC)Draper | 4-6 6-4 6-2 | | 0.82 | 12.2% | 2.2% | 52.2% | 68.1% | 41.9% | 4/9 | 1:43 |
| 12‑Jan‑1998 | Sydney Outdoor | Hard | R32 | 77 | 67 | (WC)Draper d. (Q)Sargis Sargsian [ARM] | 7-6(6) 3-6 6-1 | | 1.04 | 4.4% | 3.3% | 55.6% | 66.0% | 62.5% | 4/7 | 1:51 |
| 5‑Jan‑1998 | Adelaide | Hard | R32 | 58 | 550 | (WC)Lleyton Hewitt [AUS] d. Draper | 6-4 6-4 | | 0.69 | 5.4% | 4.1% | 51.4% | 65.8% | 47.2% | 6/9 | 1:20 |