While Manchester United were being beaten at Old Trafford, prospective new manager Erik ten Hag also departed at the last-16 stage of the Champions League as his Ajax side were beaten by Benfica.
The Dutch manager is said to be a major target for the Red Devils having led his side out of the group stages with a perfect record - but they are now out after a 1-0 loss on Tuesday.
Darwin Nunez struck late to secure Benfica a 3-2 aggregate victory, meaning Ten Hag joins fellow United-linked boss Mauricio Pochettino in falling at this stage of the competition.
In the 77th minute, Nunez rose above the Ajax defence to score from a free-kick in a rare attack for the Portuguese club, who put up a stout defensive performance at the Johan Cruyff Arena.
Benfica's veteran centre back pair of Jan Vertonghen and Nicolas Otamendi were a defensive wall that their hosts were unable to break down, despite dominating possession and constantly attacking the visitors' goal.
The Dutch club had won all their group games and, after a 2-2 draw in the first leg of the last-16 tie in Lisbon last month, were expected to ease through to the last-eight with home advantage in the second leg.
But their hopes of an extended run in the Champions League were brought to a sudden end by Benfica, who have had a poor domestic season and flounder 12 points from the summit of the Portuguese Primeira Liga.
Ajax peppered the Benfica goal in the first-half at the end of swift build-ups and multiple crosses into the penalty area, but got few of their efforts on target.
Teenager Ryan Gravenberch created an opening for himself with a strong run but fired his 36th-minute shot just over the crossbar in the best effort of the opening period.
Ajax kept up the pressure in the second-half with Brazilian winger Antony having two good chances. He put a header wide and was then foiled by a late Vertonghen tackle.
Nunez then rose high above Jurrien Timber and the on-rushing goalkeeper Andre Onana from the set piece to stun the home crowd.
Ajax could have equalised deep in stoppage time but Benfica goalkeeper Odysseas Vlachodimos pulled off a superb stop to deny Brian Brobbey, although the Ajax substitute was then ruled offside.
