With Boro preparing to face AFC Bournemouth in the Carabao Cup Round of 16 on Tuesday evening, we take a look at how Garry Monk's side have progressed so far in the competition.
Boro's tournament campaign began at the Riverside back in August, against League One Scunthorpe United.
It was a night of firsts for the Teessiders, Lewis Baker making a first start in Boro colours alongside debutants Marcus Tavernier and Connor Roberts. Lewis Wing, a late substitute, was involved with the senior side for the first time.
The trio of goalscorers were all firsts for Boro as well, Fabio and Ashley Fletcher netting either side of Baker in a comfortable 3-0 victory for Garry Monk's side.
Our next Carabao Cup tie, on the other hand, had a very familiar feel to it.
That's because Boro's third round trip to Villa Park in mid-September was a repeat of a league meeting between the sides exactly a week prior.
The first meeting had ended scoreless for the ten men of Boro, but this time out we were clear victors. Patrick Bamford bagged a brace - his his 50th and 51st career goals - in a 2-0 win.
Once again, boss Monk turned to Boro's youngsters in the competition with Tavernier and Wing involved from the start, George Miller introduced for his first team debut, and Aynsley Pears involved in the senior squad for the first time.