The Swansea-born winger formed a part of the Lilywhites' legendary double-winning squad of 1960-61, where the North London giants clinched the First Division title and FA Cup crown.
The double represented two of six major honours that Medwin won during his time with Spurs, also triumphing in the 1962 FA Cup, the 1962-63 UEFA Cup Winners' Cup and two Community Shields.
Medwin scored 72 goals in 215 matches for Tottenham across all competitions and spent seven years in North London from 1956 to 1963, having learned his trade at hometown club Swansea City.
A 30-cap Wales international, Medwin scored six goals for his nation, including the winner in a 2-1 World Cup 1958 playoff victory over Hungary, which sent the Dragons through to a quarter-final with Brazil.
The erstwhile Tottenham man played the full 90 minutes of that clash with the Selecao at right-wing, as Wales bowed out in a 1-0 defeat owing to a goal from the late Pele.
Tottenham "deeply saddened" by Medwin's death
"The Club is deeply saddened to learn of the passing of Terry Medwin, a member of our famous double-winning squad of 1960/61, who passed away this morning (Wednesday 1 May). He was 91," a statement from Tottenham read.
"A versatile forward who could play in all positions across the front line, Terry joined us from Swansea Town in April, 1956 and went on to make 215 appearances in all competitions for us, scoring 72 goals. Our thoughts are with Terry's family and friends at this impossibly sad time."
After 14 years as a professional player, Medwin's career was blighted by a broken leg - sustained in a tour match versus South Africa in 1963 - for two years before he hung up his boots in 1965.
The Wales international subsequently tried his hand at coaching, briefly taking charge of Cheshunt for one year, helping the Ambers earn promotion to Division One of the Athenian League.
Stints as a trainer at Cardiff City, Fulham and Norwich City followed for Medwin, who also spent three years as assistant manager at Swansea City from 1978 to 1981, acting as John Toshack's lieutenant.
Medwin's grandson Cameron Medwin also played professionally in Canada, representing the likes of London City, York Region Shooters, Vaughan Shooters, Toronto Lynx and Brampton United.