Centre-forward Cross played schools football with East Ham and Essex before signing apprentice forms for West Ham on 1 July 1964. He was top reserve goal scorer for the Hammers on two consecutive seasons, before making his first-team debut as a substitute for John Sissons against Burnley at Upton Park 26 August 1968 in a 5-0 thrashing of the Turf Moor outfit.

In October of the same year he had joined Leyton Orient on a two-month loan spell. After making just 8 appearances in the claret and blue shirt and scoring a single goal he was forced to drop into the lower echelons of the League with Brentford to find regular first team soccer.

The Bees’ signed him for £12,000 on 12 March 1970. He later went on a merry-go-round of London clubs and played for Fulham, who signed him for £30,000 scoring ten goals in 46 league and cup appearances for the west London club. He had a second spell at Griffin Park, and took his Bee's tally to 228 appearances and 79 goals. He then joined Millwall for £8,000.

In 1977, Cross moved to the United States to play for the Seattle Sounders of the North American Soccer League. Later to become coach at Queens Park Rangers, Tottenham Hotspur and in February 1998 teamed up with his former team-mates Harry Redknapp and Frank Lampard to become first team coach at Upton Park.

In 1979, he took the youth team manager position at Millwall. After a period on the coaching staff at Queens Park Rangers, he moved to Spurs, where he later became assistant manager to Gerry Francis. He re-joined West Ham as reserve team coach in the summer of 2001 later going on to become Hammers’ chief scout.