We welcome Burton Albion to the Riverside on Tuesday evening for the first Carabao Cup meeting between the sides since 2015.
Boro have reached the quarter final stage of the competition twice since lifting the trophy back in 2004. The first, in the 2012/13 campaign, we were edged out by then-Premier League Swansea City at the Liberty Stadium.
The second was three seasons later, and saw us defeat Burton at the Pirelli Stadium in the tournament's early stages.
But it was no easy task.
Prior to that game, the teams had only faced off once in our history, a surprise FA Cup win for the Staffordshire side back in 2011.
Another upset was on the cards here, with the Brewers led for a large chunk of proceedings thanks to an unfortunate own goal from George Friend.
Cristhian Stuani eventually levelling up for Boro, and the Uruguayan popped up again in extra time to complete the turnaround and send The Teessiders through to the third round.
Victories over Wolves and Man United followed, with Boro eventually bowing out to Everton in the last eight stage.
Although that remains the last cup encounter between our senior sides, Boro's Under-23s did play Burton's First Team in the Checkatrade Trophy earlier this year.
It was a dead rubber in terms of progressing from the group stages, but it proved to be a historic night for Boro's Academy, who claimed a first-ever Checkatrade Trophy victory thanks to 16-year-old substitute Hayden Hackney's late header.