After a goalless draw with the Red Devils, which went to extra-time, Boro claimed a memorable 3-1 win in the subsequent penalty shootout in front of 10,000 jubilant away supporters. Scroll down and flick through our picture gallery to see the side which played:
9. LW: Carlos de Pena
Now a regular at Ukrainian side Dynamo Kyiv and has made a couple of Europa League appearances this season. Photo: Shaun Botterill
10. CAM: Stewart Downing
Joined up with former Boro boss Tony Mowbray at Blackburn in the summer after his contract on Teesside expired. Has started the season well, featuring in 13 out of Rovers' 14 league games. Photo: Shaun Botterill
11. ST: Kike
Left Boro for Spanish side Eibar in 2016 after sending an emotional goodbye message to Boro fans. The striker has made seven La Liga appearances this season for a side who sit 16th in the table. Photo: Getty Images
12. Sub: Bruno Zuculini
Left Manchester City for Italian side Hellas Verona in 2017 and has since moved to back to Argentina to play for River Plate. Has recently been struggling with a thigh injury. Photo: Quinn Rooney