At just 18 years of age Gary Winram smashed two Australian records, by winning the NSW 1650 yards championship in 18 minutes:58.9s. During his brilliant swim, he also broke the Australian record for 1500m. Gary was a world class swimmer and considered one of the greatest Olympic chances for the 1956 Games in Melbourne. Winram's coach, Sep Prosser said Gary's time would have earned him first place at the Empire Games, the previous year. Although finishing a disappointing 8th in the 1500m final in 1956, Gary won a silver medal in the 1958 Empire Games 1650 yards anf Bronze in the 440 Yards.
Gary also won the junior surf race at the Metropolitan Surf Teams competition in 1953, helping North Bondi take out the top 4 places.