On this day in 1997, Boro played in an FA Cup Final for the first and so far only time in our history.
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. Gianluca Festa's header looked to have clawed Robson's men back into the game after Di Matteo's early strike, but Boro's Italian was denied by the lineman's flag.
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.
We would have to wait until 2004, at Cardiff's Millennium Stadium, to finally claim a first major trophy as we beat Bolton Wanderers 2-1 to lift the League Cup.