7‑Nov‑1983 | Taipei | Carpet | R32 | 90 | | Chris Johnstone [AUS] d. Winitsky | 7-5 7-5 | | | | | | | | | |
31‑Oct‑1983 | Hong Kong | Hard | R32 | 91 | 50 | Brad Gilbert [USA] d. Winitsky | 7-5 6-2 | | | | | | | | | |
24‑Oct‑1983 | Tokyo Indoor | Carpet | R16 | 90 | 3 | (2)Jimmy Connors [USA] d. (Q)Winitsky | 6-3 6-1 | | | | | | | | | |
24‑Oct‑1983 | Tokyo Indoor | Carpet | R32 | 90 | 79 | (Q)Winitsky d. Vincent Van Patten [USA] | 6-2 4-6 7-5 | | | | | | | | | |
17‑Oct‑1983 | Tokyo Outdoor | Hard | R32 | 89 | 13 | (1)Andres Gomez [ECU] d. Winitsky | 6-3 7-6 | | | | | | | | | |
17‑Oct‑1983 | Tokyo Outdoor | Hard | R64 | 89 | | Winitsky d. (Q)Tetsu Kuramitsu [JPN] | 6-2 6-1 | | | | | | | | | |
25‑Sep‑1983 | Maui | Hard | R16 | 95 | 77 | (6)Chip Hooper [USA] d. Winitsky | 6-4 6-7 6-4 | | | | | | | | | |
25‑Sep‑1983 | Maui | Hard | R32 | 95 | | Winitsky d. (Q)Mark Vines [USA] | 7-5 6-1 | | | | | | | | | |
12‑Sep‑1983 | Dallas | Hard | R16 | 98 | 3 | (1)Jimmy Connors [USA] d. (Q)Winitsky | 6-1 6-4 | | | | | | | | | |
12‑Sep‑1983 | Dallas | Hard | R32 | 98 | 42 | (Q)Winitsky d. Sammy Giammalva Jr [USA] | 7-6 3-6 7-5 | | | | | | | | | |
30‑Aug‑1983 | US Open | Hard | R128 | 92 | | (Q)Steve Meister [USA] d. Winitsky | 7-6 2-6 6-3 7-5 | | | | | | | | | |
15‑Aug‑1983 | Stowe | Hard | SF | | 38 | (4)John Fitzgerald [AUS] d. Winitsky | 6-4 6-3 | | | | | | | | | |
15‑Aug‑1983 | Stowe | Hard | QF | | 51 | Winitsky d. (5)Tom Gullikson [USA] | 6-1 2-6 6-3 | | | | | | | | | |
15‑Aug‑1983 | Stowe | Hard | R16 | | 96 | Winitsky d. Derek Tarr [USA] | 4-6 6-4 6-0 | | | | | | | | | |
15‑Aug‑1983 | Stowe | Hard | R32 | | 25 | Winitsky d. (2)Wojtek Fibak [POL] | 6-3 6-7 6-1 | | | | | | | | | |
1‑Aug‑1983 | Indianapolis | Clay | R64 | | 50 | (13)Diego Perez [URU] d. Winitsky | 6-0 3-6 6-1 | | | | | | | | | |
25‑Jul‑1983 | North Conway | Clay | R32 | | 56 | (16)Fernando Luna [ESP] d. Winitsky | 6-3 3-6 7-6 | | | | | | | | | |
25‑Jul‑1983 | North Conway | Clay | R64 | | 90 | Winitsky d. Jairo Velasco [ESP] | 6-2 6-2 | | | | | | | | | |
18‑Jul‑1983 | Washington | Clay | R64 | 82 | | Chris Johnstone [AUS] d. Winitsky | 5-7 6-0 6-4 | | | | | | | | | |
1‑May‑1983 | Forest Hills WCT | Clay | R32 | | 4 | (3)Guillermo Vilas [ARG] d. Winitsky | 7-5 6-2 | | | | | | | | | |
1‑May‑1983 | Forest Hills WCT | Clay | R64 | | 53 | Winitsky d. John Fitzgerald [AUS] | 6-3 6-4 | | | | | | | | | |
4‑Apr‑1983 | Houston-WCT | Clay | R32 | | 88 | Ramesh Krishnan [IND] d. Winitsky | 6-1 6-4 | | | | | | | | | |
21‑Feb‑1983 | Delray Beach WCT | Clay | R16 | | 67 | Eddie Dibbs [USA] d. Winitsky | 6-3 6-1 | | | | | | | | | |
21‑Feb‑1983 | Delray Beach WCT | Clay | R32 | | 6 | Winitsky d. (3)Jose Luis Clerc [ARG] | 6-3 3-6 6-1 | | | | | | | | | |
7‑Feb‑1983 | Richmond WCT | Carpet | R32 | | 18 | (8)Brian Teacher [USA] d. Winitsky | 6-3 6-1 | | | | | | | | | |
31‑Jan‑1983 | Philadelphia | Carpet | R64 | 87 | 69 | Guy Forget [FRA] d. Winitsky | 6-7 7-6 6-4 | | | | | | | | | |
24‑Jan‑1983 | Guaruja | Hard | R32 | 53 | | Francisco Gonzalez [PAR] d. (12)Winitsky | 7-6 2-6 6-2 | | | | | | | | | |