Despite Nani seemingly grabbing the win for United in the second half, a late Eden Hazard penalty put it to extra-time at 3-3.
Daniel Sturridge and Ramires put it at 5-3, before Ryan Giggs scored a consolation goal for United.
Liverpool also went out, with manager Brendan Rodgers' old team, Swansea succeeding in a 3-1 win at Anfield, knocking out the holders in doing so.
Norwich also pulled off an upset, scoring twice in the last ten minutes to beat Tottenham 2-1.
The full results are:
Chelsea 5-4 Manchester United (aet)
Liverpool 1-3 Swansea
Norwich 2-1 Tottenham
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