The fifth set of games were mainly played over the weekend 16–18 February 1991, with replays being played on 20 February. The
Merseyside derby went to an extra replay played on 27 February, the last FA Cup tie to go to multiple replays before a rule change the following season limited ties to one replay.
Kenny Dalglish resigned as Liverpool's manager between the two replays. Because Nottingham Forest did not win their fourth round tie until 18 February, their fifth round match was not played until 25 February with a replay on 4 March. Similarly, Arsenal were late beating Leeds United in the previous round and so played Shrewsbury Town on 27 February. Shrewsbury, Crewe Alexandra and Cambridge United, from the Third Division, were the lowest-ranked teams in the draw, with Cambridge defeating Second Division Sheffield Wednesday to progress to the Sixth Round for the second consecutive season. ==Sixth round proper==