14‑Nov‑1988 | Detroit | Carpet | QF | 127 | 133 | Leif Shiras [USA] d. Sampras | 6-4 1-6 6-3 | | | | | | | | | |
14‑Nov‑1988 | Detroit | Carpet | R16 | 127 | 8 | Sampras d. (1)Tim Mayotte [USA] | 6-3 6-4 | | | | | | | | | |
14‑Nov‑1988 | Detroit | Carpet | R32 | 127 | 201 | Sampras d. Bill Scanlon [USA] | 6-7 6-3 6-4 | | | | | | | | | |
3‑Oct‑1988 | Scottsdale | Hard | R16 | 157 | 23 | (2)Kevin Curren [USA] d. (Q)Sampras | 6-7 7-6 7-6 | | | | | | | | | |
3‑Oct‑1988 | Scottsdale | Hard | R32 | 157 | 79 | (Q)Sampras d. Jim Courier [USA] | 6-3 6-1 | | | | | | | | | |
19‑Sep‑1988 | Los Angeles | Hard | R16 | 190 | 32 | (5)David Pate [USA] d. (WC)Sampras | 6-3 7-6 | | | | | | | | | |
19‑Sep‑1988 | Los Angeles | Hard | R32 | 190 | 184 | (WC)Sampras d. (Q)Peter Doohan [AUS] | 3-6 6-3 6-3 | | | | | | | | | |
29‑Aug‑1988 | US Open | Hard | R128 | 188 | 69 | Jaime Yzaga [PER] d. (WC)Sampras | 6-7 6-7 6-4 7-5 6-2 | | | | | | | | | |
22‑Aug‑1988 | Rye Brook | Hard | R16 | 206 | 92 | Jeremy Bates [GBR] d. (Q)Sampras | 6-7 6-3 6-3 | | | | | | | | | |
22‑Aug‑1988 | Rye Brook | Hard | R32 | 206 | 39 | (Q)Sampras d. (1)Michiel Schapers [NED] | 7-5 7-6 | | | | | | | | | |
15‑Aug‑1988 | Cincinnati | Hard | R64 | 208 | 13 | (6)Brad Gilbert [USA] d. (WC)Sampras | 6-4 6-2 | | | | | | | | | |
8‑Aug‑1988 | Winnetka CH | Hard | R32 | 214 | 282 | Nicolas Pereira [VEN] d. Sampras | 7-6 7-6 | | | | | | | | | |
1‑Aug‑1988 | Seattle CH | Hard | R32 | 215 | 472 | (LL)Malcolm Allen [USA] d. (3)Sampras | 6-4 6-0 | | | | | | | | | |
18‑Jul‑1988 | Schenectady | Hard | SF | 286 | 11 | (1)Tim Mayotte [USA] d. Sampras | 6-2 7-6 | | | | | | | | | |
18‑Jul‑1988 | Schenectady | Hard | QF | 286 | 265 | Sampras d. Doug Burke [JAM] | 6-3 6-3 | | | | | | | | | |
18‑Jul‑1988 | Schenectady | Hard | R16 | 286 | 276 | Sampras d. Gianluca Pozzi [ITA] | 6-1 7-5 | | | | | | | | | |
18‑Jul‑1988 | Schenectady | Hard | R32 | 286 | 242 | Sampras d. Wolfgang Popp [GER] | 6-2 6-1 | | | | | | | | | |
9‑May‑1988 | Raleigh CH | Clay | R16 | 298 | 162 | (3)Barry Moir [RSA] d. (WC)Sampras | 7-6 6-4 | | | | | | | | | |
9‑May‑1988 | Raleigh CH | Clay | R32 | 298 | 364 | (WC)Sampras d. (Q)Eduardo Velez [MEX] | 6-3 4-6 6-3 | | | | | | | | | |
2‑May‑1988 | Forest Hills | Clay | R64 | 311 | 22 | (6)Mikael Pernfors [SWE] d. (Q)Sampras | 7-5 7-5 | | | | | | | | | |
29‑Feb‑1988 | Indian Wells | Hard | R16 | 893 | 18 | (8)Emilio Sanchez [ESP] d. (Q)Sampras | 7-5 6-2 | | | | | | | | | |
29‑Feb‑1988 | Indian Wells | Hard | R32 | 893 | 25 | (Q)Sampras d. (10)Eliot Teltscher [USA] | 7-5 6-3 | | | | | | | | | |
29‑Feb‑1988 | Indian Wells | Hard | R64 | 893 | 37 | (Q)Sampras d. Ramesh Krishnan [IND] | 6-3 3-6 7-6 | | | | | | | | | |
22‑Feb‑1988 | Philadelphia | Carpet | R64 | | 105 | Sammy Giammalva Jr [USA] d. (Q)Sampras | 6-4 6-3 | | | | | | | | | |