Twice UEFA Super Cup losers after UEFA Champions League successes – and now once as UEFA Europa League winners – Manchester United have won only one of their four appearances.
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1991: United 1-0 Crvena zvezda (McClair 67)
Political problems in Yugoslavia caused the 1991 UEFA Super Cup to be played as a one-off fixture at Old Trafford, where Alex Ferguson's United did not have it easy. Steve Bruce saw his penalty saved, while Dejan Savićević and Darko Pančev had chances to put 'Red Star' in front before Brian McClair tidied away the winner, finishing after Neil Webb's shot came back to him off a post.
1999: United 0-1 Lazio (Salas 35)
Having ridden their luck to win the 1999 UEFA Champions League final at the death, United's glory trail went cold in Monaco. Marcelo Salas struck the only goal, chesting down to volley an effort from just inside the box which United keeper Raimond van der Gouw could not get enough of his body behind. Boss Ferguson had just become Sir Alex after he was knighted on 12 June that year.
2008: United 1-2 Zenit (Vidić 73; Pogrebnyak 44, Danny 59)
United gave themselves too much to do after Pavel Pogrebnyak's ultra-close-range header was followed by a debut goal for Zenit's Danny. Wayne Rooney and Carlos Tévez did combine to set up Nemanja Vidić to score, and the Reds also had the ball in the net late on, though this time Paul Scholes was penalised for handling – and received his second yellow card in the process.
And then ...
2017: Real Madrid 2-1 Manchester United (Casemiro 24, Isco 52; Lukaku 62)
Romelu Lukaku's goal on his debut gave United a sniff of victory in Skopje, but the European champions were too strong for José Mourinho's side to end their long wait to lift this trophy again.