It was a second Wembley appearance in a little over a month for Bryan Robson's exciting Boro side, who had faced Leicester in the League Cup Final at the same venue in early April.
Ruud Gullit's Chelsea would ultimately prove too strong for the Teessiders, earning a 2-0 victory thanks to goals from Roberto Di Matteo and Eddie Newton. Defeat on the day concluded an agonising season for Boro, who had been relegated from the Premiership on the final day of the league campaign as well as losing out to Leicester in a League Cup Final replay.
Chelsea would become all-too-familiar cup final foes - having beaten Boro in the club's first Wembley appearance - the Zenith Data Systems Cup Final in 1990 - and won again here, they were also victors in Boro's second successive League Cup Final at Wembley the following year.
Boro would have to wait until 2004, at Cardiff's Milennium Stadium, to finally claim a first major trophy as we beat Bolton Wanderers 2-1 to lift the League Cup.
Take a look at photos from what remains a historic day for the club.