19‑Dec‑1983 | Adelaide | Grass | SF | 76 | 44 | (5)Mike Bauer [USA] d. (8)Drewett | 7-6 6-4 | | | | | | | | | |
19‑Dec‑1983 | Adelaide | Grass | QF | 76 | | (8)Drewett d. Leif Shiras [USA] | 7-5 6-4 | | | | | | | | | |
19‑Dec‑1983 | Adelaide | Grass | R16 | 76 | | (8)Drewett d. (Q)Greg Whitecross [AUS] | 6-3 6-4 | | | | | | | | | |
19‑Dec‑1983 | Adelaide | Grass | R32 | 76 | | (8)Drewett d. (Q)Anthony Lane [AUS] | 6-4 6-4 | | | | | | | | | |
12‑Dec‑1983 | Sydney Outdoor | Grass | R64 | 72 | 68 | Wally Masur [AUS] d. Drewett | 4-6 6-4 7-5 | | | | | | | | | |
29‑Nov‑1983 | Australian Open | Grass | R64 | 76 | 19 | (8)Anders Jarryd [SWE] d. Drewett | 6-4 7-6 6-2 | | | | | | | | | |
29‑Nov‑1983 | Australian Open | Grass | R128 | 76 | | Drewett d. (Q)John Austin [USA] | 7-6 6-1 6-4 | | | | | | | | | |
31‑Oct‑1983 | Hong Kong | Hard | R16 | 80 | 48 | Sammy Giammalva Jr [USA] d. Drewett | 6-2 6-3 | | | | | | | | | |
31‑Oct‑1983 | Hong Kong | Hard | R32 | 80 | | Drewett d. (Q)Andy Andrews [USA] | 2-6 6-1 6-0 | | | | | | | | | |
24‑Oct‑1983 | Tokyo Indoor | Carpet | R32 | 76 | 58 | Chip Hooper [USA] d. Drewett | 3-6 6-2 6-2 | | | | | | | | | |
10‑Oct‑1983 | Sydney Indoor | Hard | R16 | 74 | 20 | (5)Henri Leconte [FRA] d. Drewett | 6-1 6-3 | | | | | | | | | |
10‑Oct‑1983 | Sydney Indoor | Hard | R32 | 74 | | Drewett d. (Q)David Mustard [NZL] | 6-2 6-2 | | | | | | | | | |
3‑Oct‑1983 | Brisbane | Carpet | R16 | 75 | | (Q)Simon Youl [AUS] d. Drewett | 4-6 7-6 7-6 | | | | | | | | | |
3‑Oct‑1983 | Brisbane | Carpet | R32 | 75 | | Drewett d. David Mustard [NZL] | 7-6 6-1 | | | | | | | | | |
30‑Aug‑1983 | US Open | Hard | R64 | 80 | 14 | (13)Steve Denton [USA] d. Drewett | 6-2 3-6 6-3 6-4 | | | | | | | | | |
30‑Aug‑1983 | US Open | Hard | R128 | 80 | 64 | Drewett d. Thierry Tulasne [FRA] | 7-6 4-6 6-4 5-7 6-3 | | | | | | | | | |
15‑Aug‑1983 | Stowe | Hard | QF | 90 | | Matt Doyle [USA] d. Drewett | 4-6 6-4 7-6 | | | | | | | | | |
15‑Aug‑1983 | Stowe | Hard | R16 | 90 | 77 | Drewett d. Brad Gilbert [USA] | 5-7 7-6 6-4 | | | | | | | | | |
15‑Aug‑1983 | Stowe | Hard | R32 | 90 | 14 | Drewett d. (1)Johan Kriek [USA] | 2-6 3-1 RET | | | | | | | | | |
1‑Aug‑1983 | Indianapolis | Clay | R64 | 86 | 38 | (10)Mario Martinez [BOL] d. Drewett | 6-4 6-2 | | | | | | | | | |
25‑Jul‑1983 | South Orange | Clay | F | | 35 | Drewett d. (3)John Alexander [AUS] | 4-6 6-4 7-6 | | | | | | | | | |
25‑Jul‑1983 | South Orange | Clay | SF | | | Drewett d. Eric Korita [USA] | 6-3 6-4 | | | | | | | | | |
25‑Jul‑1983 | South Orange | Clay | QF | | 100 | Drewett d. Terry Moor [USA] | 6-3 6-4 | | | | | | | | | |
25‑Jul‑1983 | South Orange | Clay | R16 | | 63 | Drewett d. (7)Mark Dickson [USA] | 7-5 6-3 | | | | | | | | | |
25‑Jul‑1983 | South Orange | Clay | R32 | | 71 | Drewett d. Jeff Borowiak [USA] | 6-3 6-3 | | | | | | | | | |
18‑Jul‑1983 | Washington | Clay | R32 | | | Chris Johnstone [AUS] d. Drewett | 5-7 6-0 6-4 | | | | | | | | | |
18‑Jul‑1983 | Washington | Clay | R64 | | 60 | Drewett d. (10)Manuel Orantes [ESP] | 7-6 6-4 | | | | | | | | | |
11‑Jul‑1983 | Boston | Clay | R32 | | 54 | (10)Mark Dickson [USA] d. Drewett | 7-5 6-3 | | | | | | | | | |
11‑Jul‑1983 | Boston | Clay | R64 | | | Drewett d. Eddie Edwards [RSA] | 6-2 6-3 | | | | | | | | | |
4‑Jul‑1983 | Newport | Grass | QF | | 57 | (3)John Fitzgerald [AUS] d. Drewett | 6-3 7-6 | | | | | | | | | |
4‑Jul‑1983 | Newport | Grass | R16 | | | Drewett d. Vijay Amritraj [IND] | 6-4 6-3 | | | | | | | | | |
4‑Jul‑1983 | Newport | Grass | R32 | | 84 | Drewett d. (7)Nick Saviano [USA] | 6-4 7-5 | | | | | | | | | |
20‑Jun‑1983 | Wimbledon | Grass | R64 | | 70 | Rodney Harmon [USA] d. Drewett | 6-2 6-4 6-4 | | | | | | | | | |
20‑Jun‑1983 | Wimbledon | Grass | R128 | | | Drewett d. Alberto Tous [ESP] | 6-3 6-1 6-1 | | | | | | | | | |
21‑Mar‑1983 | Milan | Carpet | R32 | | 27 | Bill Scanlon [USA] d. (Q)Drewett | 6-4 6-4 | | | | | | | | | |
7‑Mar‑1983 | Tunis CH | Clay | R32 | | 90 | (6)Peter Elter [GER] d. Drewett | 6-4 6-1 | | | | | | | | | |
28‑Feb‑1983 | Cairo CH | Clay | QF | | 70 | (5)Henrik Sundstrom [SWE] d. Drewett | 6-3 4-6 6-1 | | | | | | | | | |
28‑Feb‑1983 | Cairo CH | Clay | R16 | | | Drewett d. Per Hjertquist [SWE] | 7-6 2-6 6-1 | | | | | | | | | |
28‑Feb‑1983 | Cairo CH | Clay | R32 | | | Drewett d. Igor Flego [CRO] | 6-1 6-3 | | | | | | | | | |
21‑Feb‑1983 | Kuwait City CH | Hard | R32 | | | Libor Pimek [BEL] d. (6)Drewett | 3-6 6-3 6-4 | | | | | | | | | |
10‑Jan‑1983 | Auckland | Hard | R16 | 116 | 237 | Dave Siegler [USA] d. (6)Drewett | 6-7 6-4 7-6 | | | | | | | | | |
10‑Jan‑1983 | Auckland | Hard | R32 | 116 | 239 | (6)Drewett d. Peter Johnston [AUS] | 6-3 5-7 8-6 | | | | | | | | | |
28‑Dec‑1982 | Melbourne | Grass | QF | | | (8)Craig A Miller [AUS] d. Drewett | 6-3 7-6 | | | | | | | | | |
28‑Dec‑1982 | Melbourne | Grass | R16 | | | Drewett d. Cliff Letcher [AUS] | 6-2 4-6 6-4 | | | | | | | | | |
28‑Dec‑1982 | Melbourne | Grass | R32 | | 31 | Drewett d. (2)John Alexander [AUS] | 6-3 6-2 | | | | | | | | | |