Boro handed Arsenal trip in FA Cup fifth round
Aitor Karanka's side produced a sensational performance to win 2-0 at the Etihad Stadium in round four and now face another trip to one of English football's leading clubs.
Fresh from battling from 2-0 down to win 4-2 at Premier League leaders Chelsea, Bradford City have been handed a home tie against either Sunderland or Fulham.
The winner of the replay between Cambridge United – the lowest-placed remaining team in the competition - and Manchester United faces a trip to Preston North End or Sheffield United, who also meet again next week.
Derby County and Reading have been pitted together in the only all-Championship affair to ensure at least one Football League club will be present in the quarter-finals.
There will be a minimum of two all-Premier League ties after West Brom were drawn to host West Ham and Leicester City were handed a trip to Aston Villa.
Liverpool could also face fellow top-flight opposition at Selhurst Park in the form of Crystal Palace, providing the former can make it through a replay at Bolton Wanderers.
The other fifth round tie will see the winner of Monday's match between League One Rochdale and Stoke City travelling to Blackburn Rovers, who knocked out Swansea City in round four.
The draw in full:
Crystal Palace v Liverpool or Bolton Wanderers
Arsenal v Middlesbrough
Aston Villa v Leicester City
West Brom v West Ham
Bradford City v Sunderland or Fulham
Blackburn Rovers v Rochdale or Stoke City
Derby County v Reading
Preston North End or Sheffield United v Cambridge United or Manchester United
The ties will take place over the weekend of February 14-15.