Boro have been drawn against Chelsea in the Carabao Cup semi-finals.
The Teessiders will welcome the Blues to the Riverside in the first leg, before heading to Stamford Bridge in the second.
The sides last met in the FA Cup quarter-finals last year, a 2-0 victory for the Londoners, while the most recent League Cup meeting was the final of the competition in March 1998 which Chelsea won by the same scoreline.
Liverpool will take on Fulham in this season's other semi-final.
First leg ties are due to be played week commencing 8 January, and the return legs week commencing 22 January.