Here are the biggest FA Cup upsets from each season since 2012.
The Championship club faced Tottenham Hotspur at the Riverside Stadium and looked like they could comfortably claim the victory on a number of occasions inside 90 minutes.
However, they took Antonio Conte’s side to extra-time and it was young Josh Coburn that shattered Spurs’ hopes.
The teenager was brought on with 96th minutes gone and only 11 minutes later he was celebrating in front of the home fans after he had scored the only goal of the game.
Middlesbrough’s victory is one of a number of upsets this season and they have become a guarantee every year now.
Here are some of the biggest FA Cup upsets from each of the last ten seasons...
1. Newcastle United 0-1 Cambridge United - 8 January 2022
League One side Cambridge United stunned the Magpies when a second half goal from Joe Ironside knocked them out of the FA Cup. They were then beaten 3-0 by Luton Town in the fourth round.
2. Crawley Town 3-0 Leeds United - 10 January 2021
Crawley Town shocked Leeds when they tore apart Marcelo Bielsa’s side last season. Former TOWIE star and Heart radio presenter Mark Wright even made an appearance.
3. Shrewsbury Town 2-2 Liverpool - 26 January 2020
While they didn’t win and Liverpool won the second leg, Shrewsbury Town’s draw against Liverpool was a brilliant result for the League One club. The Reds had been 2-0 up until a brace from Jamie Cummings set New Meadow into hysterics.
4. Newport County 2-1 Leicester - 6 January 2019
Goals from Jamille Matt and Padraig Amond handed Newport the victory over Leicester City in their sixth successive season in League Two.