Leslie Dennis Medley was born in Lower Edmonton, London, England, on September 3, 1920. He started his soccer career with the Edmonton Schools team. Les played in a schoolboy international for England against Scotland at Hampden Park in Glasgow in 1935.

The two-footed outside left signed a professional contract with Tottenham Hotspur in February 1939. When World War II broke out Les joined the Royal Air Force. In 1944 Les attended the R.A.F. Navigation School at Hamilton in Ontario. In May 1944 his R.A.F. team played to a 3-3 tie with the American Soccer League All-Star team in New York. A crowd of 4,000 watched Les score two goals. In September 1944 Les and his R.A.F. team returned to New York and played against a selected team from New York Americans and Brookhattan. The airmen lost 1-3 in front of 5,000 fans at Starlight Park.

While with the R.A.F. Leslie married Thelma Morris of Hamilton, Ontario. After the war the couple settled in England and Les rejoined Tottenham. However, his wife struggled with ill health in England. On October 8, 1946, Les scored against Burnley in 1-1 tie in a Football League match watched by 44,351 at White Hart Lane.

The couple returned to Canada in October 1946. On November 5, 1946, Les signed for Toronto Greenbacks. He made his debut for the Greenbacks on November 9 in a challenge match. The Greenbacks played in both the National Soccer League and the North American Professional Soccer League in the 1947 season.

Les and Thelma became parents of their son, Steven, in 1947.

In November 1947 Les played for Ulster United against the New York All-Stars at Sterling Oval. The match was watched by 2,500 fans and the game ended in a 3-3 tie. Les score done of the goals for Ulster United.

Les and his family returned to England in January 1948. After a 17-month absence he returned to Tottenham Hotspur and made a comeback in a F.A. Cup semi-final game against Blackpool at Villa Park, Birmingham, on March 13, 1947. Blackpool won 3-1 after extra-time.

He starred on the Tottenham’s left-wing when the club won the 1949-50 Second Division championship. The club won the First Division championship in the 1950-51 season. In the 1951-52 season Tottenham finished as runners-up to champions Manchester United in the First Division.

The 5’8 and 154 lbs forward was picked for the English Football Association team to tour the United States and Canada in the summer of 1950. He played in six full international games for the English National Team, making his debut against Wales in 1950.

Les returned to Canada again in the summer of 1952 when Tottenham toured North America. On June 19 he scored one goal and had two assists as Tottenham defeated the Montreal All-Stars 8-0 in front of 6,000 fans in Montreal.

The 1952-53 season was a troubled one for Les. He started the season with injuries, first having an abscess in his ear and then going down with food poisoning. To everyone’s surprise Les was put on the transfer list by Tottenham in November 1952. His price was said to be £20,000. In May 1953 he decided to retire from soccer and sailed with his family to Canada at the end of the same month. His first destination was Hamilton but he intended to go to Toronto to try to get a job there.

In June 1953 he joined Ulster United. He helped the Redhanders to a second-place finish in the National Soccer League in his first season with the club. He was the player-coach of Ulster United when they won the 1954 National Soccer League play-off championship.

Les played on numerous All-Stars teams while in Canada. He would often be invited to play on All-Star teams in other regions as well, appearing several times in New York.

In the 1955 season Ulster United finished in second place in the NSL final standings. The Redhanders won the 1955 Arnold Cup, emblematic of the NSL play-off championship, by beating Polish White Eagles in the final.

On May 21, 1955 Les played for the Ontario All-Stars against touring English team Huddersfield Town. Huddersfield Town won 3-1 in front of 5,600 fans at Varsity Stadium.

Les was the player-coach of Wanderers and Randfontein in South Africa in the end of the 1950’s.

Leslie Medley passed away on February 22, 2001, in Canada.