Nicholson got his start with Spurs in 1936 working for the grounds staff. In 1938, he signed a professional contract with them and spent his entire career with the London club, making 214 league appearances before hanging up his boots in 1955.
He joined the Tottenham coaching staff in 1955 and was the first-team coach in 1958 when then-manager Jimmy Anderson was sacked. At the time, Spurs were sixth from bottom of the First Division table. They finished the season at fifth from bottom, but Nicholson eventually turned the club around, winning the Double in 1961.
Nicholson went on to become one of Tottenham's most successful managers, winning two more FA Cups (1962, 1967), two League Cups (1971, 1973), the European Cup Winners' Cup (1963), and the UEFA Cup (1972). He took Spurs to the 1974 UEFA Cup Final, where they lost to Feyenoord, and resigned shortly afterward.
He was inducted into the English Football Hall of Fame in 2003 and passed away the following year.
Nicholson's 10-4 debut victory over Everton was a club record at the time, but was broken the next season when Spurs defeated Crewe Alexandra 13-2 in the FA Cup on 3 February 1960.