Manchester United will play seven-time Champions League winners AC Milan in the last 16 of the Europa League.
AC Milan, who sit second in Serie A, are yet to win the competition while United’s only triumph was in 2017.
Arsenal, finalists in 2019, face Greek side Olympiakos, who knocked them out in the last-32 stage last year.
Tottenham will play Croatian side Dinamo Zagreb while Rangers have been drawn against Czech side Slavia Prague, who defeated Leicester City this week.
The eight last-16 ties will be played on 11 and 18 March.
Former Manchester United striker Zlatan Ibrahimovic looks set to return to Old Trafford in the second leg, when the two sides will meet for the 12th time in European competition – all previous meetings having been in the Champions League.
Rangers, who recorded a 9-5 aggregate win over Royal Antwerp on Thursday to reach the last 16 for the second successive season, will take on Slavia Prague for the first time.
Tottenham opponents, Dinamo Zagreb, who will be at home for the first leg, have a dismal record against English opposition.
They have been on the defeating side nine out of the last ten matches with the sonly victory coming in a 2-1 win over Arsenal in the Champions League group stage in 2015.