Greaves began his professional career at Chelsea in 1957, and played in the following year's FA Youth Cup final. He scored 124 First Division goals in just four seasons before being sold on to Italian club A.C. Milan for £80,000 in April 1961. His stay in Italy was not a happy one and he returned to England with Tottenham Hotspur for a fee of £99,999 in December 1961. Whilst with Spurs he won the FA Cup in 1961–62 and 1966–67, the Charity Shield in 1962 and 1967, and the European Cup Winners' Cup in 1962–63; he never won a league title but did help Spurs to a second-place finish in 1962–63. He moved to West Ham United in a player-exchange in March 1970 and retired the following year. After a four-year absence he returned to football at the non-league level, despite suffering from alcoholism. In a five-year spell he played for Brentwood, Chelmsford City, Barnet, and Woodford Town before retiring for good in 1980.