Goals from Patrick Bamford and Kike Garcia secured a 2-0 win for Aitor Karanka’s side against Manuel Pellegrini’s reigning Premier League champions. Scroll down and flick through our picture gallery to see the Boro team which played that day and what has happened to them all since:
13. Sub: Kike
Left Boro for Spanish side Eibar in 2016 and has played regularly for the La Liga side since. Photo: OLI SCARFF
14. Sub: Yanic Wildschut
The Dutch winger represented several English sides, including Wigan, Norwich, Cardiff and Bolton, after leaving Boro in 2016. Wildschut, 28, signed for Israeli club Maccabi Haifa at the start of this season. Photo: Getty Images
15. Manager: Aitor Karanka
The Spanish boss remains out of work after leaving Nottingham Forest a year ago. Photo: Alex Livesey