Boro will travel to Bolton Wanderers in the second round of the Carabao Cup.
The Teessiders beat Huddersfield to set up the tie, while Bolton edged out Barrow.
Our last trip to Wanderers was a 2-0 win in the Sky Bet Championship back in 2019, while the last League Cup meeting between the sides was, of course, the 2004 final.
Round Two ties are set to be played week commencing 28 August.