In 1893 the team exceeded the exploits of their fore-runners and defeated Chatham in winning the Kent Senior Cup. Ashford had been the beneficiaries of a bye prior to the final – in the semi-final they were due to meet the West Kent Regiment but the West Kent's were shipped out to Ireland before the match took place. Scorers for United in the 2–0 win were Archie Munro and Frank Young. A few months afterwards, in October 1893, in an 1893–94 FA Cup first round qualifying match Ashford United suffered their record defeat: a 12–0 loss to Woolwich Arsenal (and an all-time equaling biggest goal difference win by Arsenal). The tie was not without controversy as before the match it was reported in the Kentish Independent Newspaper that Arsenal, as a team playing at a higher level (they had that season joined the Football League Second Division), expected a one-sided victory and had openly offered Ashford £20 and the promise of a friendly match against their second team in Ashford if they would scratch from the tie: the offer was not accepted.