After an underwhelming first full season in charge, where the club only avoided relegation on goal difference, an improved second season saw the club miss out on a play-off spot by just one place, and they also eliminated then-Premier League Leeds United from the FA Cup.
A dire third season cost Fenwick his job however, and he left with the Club bottom of the Division One table.
He started his career in Crystal Palace F.C. and went on to play for major clubs such as Queens Park Rangers and Tottenham Hotspur. During this period he was a regular for the England national football team.
He holds the English record for most yellow cards (three) in a single tournament, which he achieved in the 1986 FIFA World Cup. During that World Cup, Fenwick was also noted for being passed by Diego Maradona as Maradona scored the Goal of the Century.
After 1990, it gradually became clear that Fenwick had witnessed his best days as a footballer. He was sent on loan to Leicester City before getting a permanent move to Swindon Town, a newly promoted FA Premier League team. His first season (1993-94) saw Swindon winning only 5 games of a total 42, conceding 100 goals and being relegated. Fenwick played 26 games during this season, and was noted for breaking the leg of Paul Warhurst — a photograph revealed that Fenwick was smiling at the incident. He played only two games the following season, was released and ended his playing career shortly thereafter.
Following in the footsteps of many former players, Fenwick decided to try a managerial career. In 1995 he replaced Jim Smith as manager for Portsmouth F.C. He was sacked in 1998. His most recent manager job was at Northampton Town in 2003, where he only lasted for 7 games. Fenwick's first game saw a 1-0 lead turn into a 2-1 defeat away to Blackpool. The next five games saw just two drawa and three more defeats. His last game in charge was against Bristol City. The 2-1 defeat saw calls for his departure from fans and he left the post the following Monday. He was replaced by Martin Wilkinson.
Fenwick has spent a considerable amount of time in the Caribbean nation of Trinidad and Tobago over the past few years. He has enjoyed a great degree of managerial success there, winning the country's professional football league and a variety of cups. He is currently the manager of football club, CL Financial San Juan Jabloteh, in the Trinidad and Tobago Pro League.