The Red Devils were eliminated from this season's edition of the competition after Middlesborough cruised to a famous win via a shootout.

Manchester United's woes in cup competitions continued on Friday night with the Red Devils suffering yet elimination in their run-in for silverware. The Red Devils were sent packing out of this season's FA Cup after losing 8-7 on penalty shootout against Middlesborough at Old Trafford.

The epic Round of 16 clash was not short of drama although the tale could have been relatively different had United been more clinical with the numerous chance that fell their way. Having dominated proceedings right from the word go, the hosts were gifted a golden opportunity to break the deadlock by being awarded a penalty following a foul on Paul Pogba in the Middlesborough penalty area.

The usual taker Bruno Fernandes stepped aside and handed the honor to compatriot Cristiano Ronaldo who missed his attempt in the 20th minute. Five minutes later, Jadon Sancho fired Ralf Rangnick's men into the lead by cutting in from the left and bending home a low curler for the first goal of his return.

It was almost another routine display for the Old Trafford in the second half but a controversial equalizer scored by Matt Crooks in the 64th minute changed the dynamics. There was a case of a handball in the build-up of the goal but the Video Assistant Referee ruled out the calls and awarded the underdogs their leveller which they held onto right till the end.

With both sides failing to produce a goal after 30 minutes of extra time, the game was forced to penalty shootouts where Anthony Elanga produced the first miss after 14 successful kicks. The final result meant that for the first time since the defeat to Swansea in 2014, Manchester United have been knocked out of the FA Cup fourth round or earlier.