In December 1987, Fenwick was again signed by Terry Venables for Tottenham Hotspur, for a fee of £550,000 and went on to make 93 appearances for Spurs, scoring eight times all from the penalty spot in just one season, 1988–89. In 1990–91 Fenwick had a loan spell at Leicester city (eight appearances 1 goal), after which he returned to Spurs halfway through the season. A broken ankle ruled him out of their victory in the 1991 FA Cup Final. In 1993 he moved on to Swindon Town.