One could not begrudge AC Milan leaving Old Trafford with a draw in this Europa League last-16 first leg. For it was the Italian side who played the better football, were the most front-footed and created the greater number of chances.
What will have irked Manchester United, however, was that the visitors’s equaliser came in the second minute of second half stoppage-time. Just as Ole Gunnar Solskjaer thought his team had managed a valuable single goal advantage to take to Milan next week, the Rossoneri snatched an away goal.
Story of the game
There is a lot of symmetry between these two sides currently. Not only are they facing each other in the Europa League but they are both in second place in their respective leagues behind their city rivals. Also they could both do with a trophy.
Therefore, this competition is a useful route to such silverware and it was an injury-ravaged Milan side that turned up this meeting. Stefano Pioli was without six first team players, including captain Alessio Romagnoli and strikers Mario Mandzukic and Zlatan Ibrahimovic, who played for United for two seasons.
Therefore there were big boots for 21-year-old Rafael Leao to fill but within five minutes he had already found the net following a ball over the top of the United defence. The Portuguese striker was offside, however, and the early scare for the home side was negated.
Solskjaer had selected a strong side with Anthony Martial playing centrally with Mason Greenwood and Dan James flanking him. The Frenchman forced Gianluigi Donnarumma to palm his early effort over the crossbar but that was United’s only chance in the opening period as it was mainly one-way traffic.
Milan had another goal disallowed when Franck Kessie controlled a throw in before conjuring a fine strike across Dean Henderson. It was a lovely shot but closer inspection showed that the midfielder had partially used his arm to control the ball - purists will have been cursing that the goal was unable to stand.
Still that did not deter the visitors, and neither did it wake up United. A well-worked move down the right ended with Rade Krunic seeing a shot deflected which made it an easy collection for Henderson.
Yet, the clearest legitimate chance of the half fell United’s way. Bruno Fernandes headed on a corner from Alex Telles, the ball travelled to the back post where Harry Maguire somehow shinned an attempt against the post from no more than a yard out. The ball flew back away from Donnarumma’s goal and Maguire was left startled by his incredible miss.
Solskjaer had cut an anxious figure for much of the first half and was forced into a half time change with Martial not able to return to action and thus Amad Diallo coming on for his debut. There are big expectations of the 18-year-old and within five minutes of entering the fray he demonstrated why.
It was great vision from Fernandes to lift a ball over the Milan backline, but Diallo’s work was the most noteworthy. He drifted in between Diogo Dalot, on loan at Milan from United, and Fikayo Tomori, on loan from Chelsea, and facing away from goal, back-headed the dropping ball over the 6ft 5 Milan goalkeeper. It was great awareness and execution from the young striker.
With the lead, which had come against the run of play, United had to repel further Milan pressure. Maguire blocked a fizzing shot from Brahim Diaz, Henderson parried Kessie’s effort while Krunic couldn’t head Davide Calabria’s cross on-target.
Knowing how valuable a 1-0 victory would be, Solskjaer made changes and reorganised to stiffen up his side. Fred, Luke Shaw and Brandon Williams all came on as United moved to a back-five and three-man midfield. It worked in that he saw the home side through into stoppage-time, but couldn’t see them home.
Krunic delivered a corner from the left and up leapt Simon Kjaer to power a header into the United net. It was just above Henderson, who got a hand to it, but he couldn’t keep it out and meant United conceded their first goal in five games and the Danish centre-back had his first goal for the club.
Pioli's side were worthy of their goal but the circumstances of its arrival will not sit well with United whose task in the second leg became that bit harder with the late equaliser.