The Debenhams Cup was one of several short-lived football competitions introduced in the 1970s and 1980s, along with the Watney Cup, Texaco Cup, Anglo-Scottish Cup, the Super Cup and Full Members Cup. It lasted for just two seasons (1976-77 and 1977-78) and was competed for between the two sides from outside the top two divisions of the Football League to have progressed furthest in the FA Cup. If teams had made the same stage of the competition, a system was in place (beginning with replay eliminations being superior to going out at the first attempt) to determine which two would play in the Debenhams Cup - one of the first sponsored competitions in English football. This was the first time a sponsor had been associated with the FA Cup.
The first season (1976-77) saw Football League Division Three sides Port Vale and Chester meet. They had both reached the fifth round before losing to Aston Villa and Wolverhampton Wanderers respectively. Coincidentally, if the competition had been played 30 years earlier during the 1946–47 season, Chester and Vale would have again been the finalists.
The games were played at the end of the campaign, shortly after a league meeting between the sides at Vale Park, which was to host the first leg. Goals from Neil Griffiths and Ken Beamish gave Vale a 2-0 victory that left them as firm favourites to win the trophy. But on a memorable night at Sealand Road, Stuart Mason, David Burns, Neil Griffiths (own goal) and Ian Howat found the net for Chester to give them a 4-1 victory on then night and a 4-3 success on aggregate. It was their first national trophy.