Real Madrid coach Jose Mourinho marked his 100th Champions League game with a 1-1 draw at Manchester City on Wednesday that sent his side into the last 16 at City’s expense. City had to win to stand any chance of going through, so although Sergio Aguero’s 73rd-minute penalty cancelled out Karim Benzema’s early opener, the hosts went out in the group phase for a second successive season. Madrid had Alvaro Arbeloa sent off, but with eight points — three less than Group D leaders Borussia Dortmund — they cannot be caught by either Ajax or City, who had not lost in their 19 previous European home games. “This Champions League is worse than last season,” said City coach Roberto Mancini. “We have only three points after five games. We did some mistakes also, because this group was very difficult and we started the group with a (3-2) defeat against Madrid in Madrid when we were 2-1 up with four minutes to go. “Everything was complicated after that result. Real Madrid and Borussia deserved to go through, because they played better than us.” The English champions trail Ajax by a point and therefore must win at Dortmund in their final group fixture and hope the Dutch side lose in Madrid if they are to secure the consolation prize of a Europa League berth. Mourinho, the youngest coach to reach the 100-match milestone, is now a step closer to delivering an elusive 10th European Cup to the Spanish champions, who have already fallen eight points off the pace in La Liga. “With the players at their (City’s) disposal, it’s amazing they’ve been eliminated in the group stage two years running,” said Mourinho. “They put us under pressure, then there was the penalty and the sending off. City had all their attacking options, and we had just 10 men, but we held on, we resisted and we managed to control the game.” Mancini elected to deploy a three-man defence at the Etihad Stadium, but the home side’s defenders did not seem comfortable with the system and Madrid were quick to profit. In the 10th minute, Angel di Maria was given space to cross from the right and his centre found the unmarked Benzema, who cantered in behind Maicon to beat Joe Hart on the volley from close range.