A prolific scorer for Spurs in the lower teams at the club, Roy Woolcott only made one appearance in the first team before moving on to play out his career in the lower leagues.
A fearless striker who showed a determination to win aerial balls, having a good record of scoring with headers, Roy's career started at Leyton based Eton Manor, before he was signed by Tottenham in February 1968. Played in one first team match for Tottenham, but he could not keep out the big money Spurs forwards of the time.
Consigned back to the reserves, Ray went out on loan to Gillingham in early 1972 and did well scoring five goals in a 13 match run with the Gills in Division 4, but he did not stay at Priestfield, returning to the club who released the striker. He moved to play with non-league Chelmsford City in the summer of 1972 until a knee injury finished his career with the Clarets. Gained notoriety in the FA Cup run of 1972-73, when he scored eight goals in four games (seven of those with his head), including the City consolation in the Third Round 1-3 defeat by Ipswich Town. It was a good season for Roy, who got 39 goals that season, but injury struck the following year and Woolcott only featured in 18 games before having to retire.
Still holds the club record at Chelmsford for scoring in nine consecutive games from Boxing Day 1972.