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:
1. GK: Jamal Blackman
This was Blackman's only appearance for Boro following his loan move from Chelsea. The 26-year-old is still a Blues player but has been loaned out to seven separate clubs since his spell on Teesside. He's now playing for Rotherham in the Championship. Photo: Getty Images
2. RB: Ryan Fredericks
The right-back moved from Tottenham to Bristol City following his loan spell at Boro. Fredericks, 27, then made over 100 appearances for Fulham before moving to West Ham in 2018. Photo: IAN KINGTON
3. CB: Daniel Ayala
Ayala spent seven memorable years at Boro before leaving the Riverside in June. After turning down a new contract at the Riverside, the 29-year-old joined Blackburn earlier this month. Photo: Getty Images
4. CB: Kenneth Omeruo
After a couple of loan spells in Turkey, Omeruo, now 26, left Chelsea permanently in 2019 to join Spanish club Leganes who were relegated from La Liga last season. Photo: Getty Images