 A winger, Cockram joined Tottenham Hotspur as a schoolboy in 1975 and went on to make two first team appearances for the "Lilywhites" towards the end of the 1983–84 season.He was released at the end of the 1984–85 season and a two-year period followed as a football nomad, which included short periods playing for Bristol Rovers and Farnborough Town and two spells in the United States.A move to Isthmian League Premier Division club St Albans City during the latter part of the 1986–87 season, in a bid to return to fitness following an achilles injury, proved to be the turning point in Cockram's career.