Namesakes
Australian Prime Ministers:
1 prime minister
John Howard (a.k.a. Winston) 1996-2007 
British Prime Ministers:
1 prime minister
Winston Churchill 1940-1945; 1951-1955
Fictional Characters from Books:
1 character
Winston Smith 1949 Nineteen Eighty-Four
Fictional Characters from Television:
1 character
Winston Williams 2017 13 Reasons Why
Hall-of-Famers:
1 football
(football) Winston Hill 2020
New Zealand Prime Ministers:
1 prime minister
Geoffrey Palmer (a.k.a. Winston) 1989-1990
Nobel Prize Winners:
1 literature
(literature) Winston Churchill 1953
Notable Actors and Entertainers:
3 actors, 1 presenter
Wink Martindale 1933-
Winston Ntshona 1941-2018
Jason Winston George 1972-
Winston Duke 1986-
Notable Athletes:
1 soccer
(soccer) Winston Bogarde 1970-
Notable Writers:
1 author
Winston Graham 1908-2003
Olympic Medalists:
2 silver, 1 bronze
(silver) Clarence Oldfield (a.k.a. Winston) 1920 4x400 m relay
(silver) Chuck Chapman (a.k.a. Winston) 1936 basketball
(bronze) Harry Jerome (a.k.a. Winston) 1964 100 m
Tony Award Winners:
1 actor
(actor) Winston Ntshona 1975 Sizwe Banzi is Dead