Scott Robinson brought short-term success during his tenure as manager in 2016/17, leading the club to their most famous moment in December 2016 when they defeated Premier Intermediate League side Dundela F.C.

However, at the end of the season after a disappointing league campaign several players left for pastures new and Robinson followed, leaving the Town to rebuild again.

On 24 June 2022, Fivemiletown ended an eleven-year wait for a trophy when they defeated Oxford Sunnyside 2–0 in the Marshall Cup final in Armagh.

The ex Manchester United keeper is undoubtedly the towns most famous ex player, having won the FA Cup and Premier League with the Red Devils.

Dermott McCaffery- The ex Hibernian and Falkirk Defender began his career with Fivemiletown United before moving on to Dunbreen Rovers.

Lee Bradbury the former Manchester City and Portsmouth striker played briefly for Fivemiletown during the 1990s when stationed in Northern Ireland with the British Army Simon Yeo the former Lincoln City striker played briefly for Fivemiletown during the 1990s when stationed in Northern Ireland with the British Army.