He made his debut when starting their 1–1 away draw with Maidstone United on 6 August 2016, in the opening match of 2016–17. According to Dave Flett of "The Press", Fenwick found the "going tough in attack", and was substituted for Richard Brodie in the 84th minute. He was an unused substitute as York beat Macclesfield Town 3–2 at Wembley Stadium in the 2017 FA Trophy Final. He was released by York at the end of the 2016–17 season. Fenwick signed for National League North club Darlington on 4 August 2017 after a successful trial. After making four substitute appearances in 25 days, he left the club by mutual consent. He signed for Maltese Premier League club Naxxar Lions, and made his debut on 10 September 2017, starting in a 0–0 away draw with Valletta. After four goals from twelve league appearances and two goals in the Maltese FA Trophy, Fenwick was released by mutual consent on 2 January 2018 because he wanted to return home. Fenwick signed for National League South club Chelmsford City on 9 March 2018. He scored a hat-trick of penalties for Chelmsford on 9 April in their 4–2 win against Whitehawk, becoming the first player in the history of the club to do so. Five days later, Fenwick scored a hat-trick of penalties for the second consecutive match, scoring all four Chelmsford goals in a 4–2 win against East Thurrock United. On 13 May 2019, Chelmsford announced the departure of Fenwick. On 14 June 2019, Fenwick returned to North East England, signing for Blyth Spartans. York City