Manchester City’s underwhelming Champions League campaign ended with a lacklustre 1-0 defeat at Borussia Dortmund.
Julian Schieber’s second-half finish from close range was enough to see off the visitors, with the German side enjoying the better of the scoring chances.
The result means Roberto Mancini’s side finish bottom of Group D without a win, the first time a Premier League side has ever failed to win a group match.
It took until the 12th minute for the first shot on target as Oliver Kirch drove straight at Joe Hart from 20 yards.
The visitors eventually fashioned an opening of their own, as Edin Dzeko slid the ball across the six-yard box looking for Carlos Tevez, but Marcel Schmelzer was able to snuff out the danger.
Dortmund were on top and perhaps should have scored when, first, Marco Reus cut into the area and blasted a left-footed effort towards Hart’s near post, which the England international managed to tip on to the woodwork and behind.
City nearly went in front straight after the restart when Dzeko met Samir Nasri’s cross, heading straight at the goalkeeper when he looked odds-on to score.
Perisic then, again, forced a save from Hart, meeting Kirch’s cross with a rasping volley from the left-hand side of the area, which the City goalkeeper had to palm over the bar before being called into action by denying Kevin Grosskreutz with an excellent one-handed stop low at his near post.
Just after Aguero was introduced by Mancini, the deadlock was finally broken in the 57th minute as the hosts took a deserved lead. Substitute Jakub Blazczykowski burst down the right and slid an excellent cross into the path of Schieber, who arrived at the far post to poke the ball into the net.
City switched to a back three with the introduction of Mario Balotelli and Pablo Zabaleta, as Tevez forced a save from Weidenfeller.
Moritz Leitner then had a superb chance to make it two after the impressive Blazczykowski pulled back, but the midfielder could only steer his effort wide.
Substitute Robert Lewandowski then brought out the best in Hart after shooting from a tight angle, before Weidenfeller saved a left-footed Aguero strike at the other end.
Meanwhile, at the Santiago Bernabeu, Real Madrid thrashed Ajax 4-1.
Cristiano Ronaldo opened the scoring in the 13th minute after some good work from Karim Benzema, before Jose Callejon doubled the hosts’ lead at the half-hour mark.
Kaka then made it three after the break, only for Derk Boerrigter to peg one back after 60 minutes. However, Callejon restored Madrid’s three-goal lead in the closing minutes.