Real Madrid, Arsenal qualify into the last 16

Karim Benzema scores the opener

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."

Arsenal 2 - 0 Montpellier

Arsenal midfielder Jack Wilshere fired the Gunners into the last 16 of the Champions League as his first goal for two years inspired a 2-0 win over Montpellier on Wednesday.

Wilshere had gone 725 days without a goal, since he netted against Aston Villa in November 2010, after being sidelined for 14 months with foot and knee injuries.

But the England international finally got back on the scoresheet with a cool finish early in the second half against the French champions and Lukas Podolski's stunning volley soon after sealed a vital victory at the Emirates Stadium.