A packed-out away end watched Boro come from behind twice after Adam Reach cancelled out Jordan Rossiter’ opener.
Liverpool retook the lead through Suso in extra-time before a Patrick Bamford penalty in the 120th minute resulted in a memorable shootout which Liverpool won 14-13.
Scroll down and flick through our gallery to see who played that night and where they are now:
5. LB: George Friend
Friend, 32, built a special bond with Boro supporters during his eight years at the Riverside but left the club for Birmingham this summer when his contract expired. Photo: Getty Images
6. CM: Adam Clayton
Another long-serving Boro player who has departed over the last few months. Clayton, 31, also moved to Birmingham where he has been reunited with former Boro boss Aitor Karanka. Photo: John Powell
7. CM: Grant Leadbitter
Boro's former captain was given compassionate leave by Sunderland to deal with some personal issues last season. The 34-year-old has returend to training with the Black Cats and played 90 minutes against Oxford at the weekend. Photo: Alex Livesey
8. RW: Albert Adomah
The likeable winger returned to Nottingham Forest in June after a loan spell with Cardiff in the second half of last season. Adomah, 32, wanted to stay in South Wales for Cardiff's final few fixtures last season but was forced to return to his parent club. Photo: Alex Livesey