After our fourth round trip to Old Trafford was confirmed, here's a look back at five of our favourite cup ties with the Red Devils...
Manchester United 0 Boro 0* (Boro win on pens) - October 2015
An emotionally charged night which saw 10,000 travelling Teessiders light up Old Trafford in a stunning show of support for steelworkers of the region, many of whom who had lost their livelihoods. On the pitch, Boro put in a suitably steely showing and were unlucky not to beat the Red Devils in normal time.
Instead, the match went to penalties where goalkeeper Tomas Mejias was the hero of the hour, keeping out spot kicks from Wayne Rooney and Ashley Young to secure Boro a famous upset.
Middlesbrough 2 Manchester United 2 - March 2007
Goals from Wayne Rooney and Cristiano Ronaldo were required to take Gareth Southgate’s Boro to a quarter-final replay. Rooney had fired the Red Devils in front, but Lee Cattermole and George Boateng netted either side of the break to swing the tie in Boro’s favour.
But Ronaldo settled scores with a second half penalty after Boateng had handled in Boro’s area, taking the contest to a replay which Manchester United would edge by virtue of another spot-kick from the Portuguese forward. James Morrison was not best pleased…
Middlesbrough 2 Manchester United 0 - January 2002
Late goals from Noel Whelan and Andy Campbell saw Boro boss Steve McClaren get one over his old employers in this fourth round tie. Indeed, Sir Alex Ferguson had announced his plans to retire at the end of this season, so the match could have proved to be his FA Cup swansong - but that decision was soon reversed by the Scot.
Boro, meanwhile, would reach the semi-finals of the competition that season, bowing out to Arsenal in a tight game decided by a fluke own goal from Gianluca Festa.
Manchester United 2 Middlesbrough 1 - March 1992
Soon-to-be-promoted second-tier Boro gave Manchester United an almighty scare in this League Cup semi-final second leg at Old Trafford. The first was a goalless draw at Ayresome Park, and 10,000 Boro fans travelled to Manchester to back their team in miserable conditions.
There was a goal for each side from Lee Sharpe and Bernie Slaven, but extra time was required to separate the sides. Only the heroics of ex-Boro man Gary Pallister and his goalkeeper Peter Schmeichel kept the Red Devils level, before Ryan Giggs popped up with a late winner to break Teesside hearts.
Middlesbrough 2 Manchester United 1 - January 1971
United were a very familiar foe for Boro in the early ‘70s, with no fewer than 10 cup ties between the sides in the space of five years.
This one was a memorable victory for Boro at a snow-covered Ayresome Park, over a side including the likes of Bobby Charlton, Denis Law and George Best. Hugh McIlmoyle and Derrick Downing were Boro’s goalscoring heroes, Best netting at late consolation for the away side.