The two sides haven’t met since the north-east side were relegated from the Premier League in 2009; Boro actually beating Liverpool at the Riverside that season. The last meeting at Anfield earlier in that season saw late goals from Jamie Carragher and Steven Gerrard grab a 2-1 win.
Middlesbrough qualified for the third round after defeating Preston 3-1 on Tuesday night. They’ve won two and lost two of their opening Championship matches so far.
Boro are currently managed by former Real Madrid defender Aitor Karanka.
The match will be played the week commencing September 22nd – prior to the Merseyside derby the following Saturday lunchtime.
Liverpool last won the competition in 2012 when Kenny Dalglish‘s side beat Cardiff City.
Chelsea v Bolton Wanderers
Arsenal v Southampton
West Bromwich Albion v Hull City
Crystal Palace v Newcastle United
Leyton Orient v Sheffield United
Cardiff City v AFC Bournemouth
Sunderland v Stoke City
Derby County v Reading
Liverpool v Middlesbrough
Milton Keynes Dons v Bradford City
Manchester City v Sheffield Wednesday
Burton Albion v Brighton and Hove Albion
Swansea City v Everton
Shrewsbury Town v Norwich City
Fulham v Doncaster Rovers
Tottenham Hotspur v Nottingham Forest