Manchester City was eliminated from the Champions League on Tuesday with a 1-0 loss to Borussia Dortmund, while Paris Saint Germain and Schalke 04 clinched first place in their respective groups.
The defending Premier League champions exited Champions play in the group stage for the second year in a row.
Finishing fourth in Group D, City was denied even the poor consolation of a Europa League berth.
Borussia won the group with 14 points, three more than Real Madrid, who thumped Ajax Amsterdam 4-1 on Tuesday.
The top two clubs in each group advance.
PSG took first place in Group A thanks to a 2-1 triumph over Porto, which came into Tuesday's match with a 1-point lead over the French side.
Dinamo Zagreb and Dynamo Kiev battled to a 1-1 tie as the Croatian club salvaged one point on its way out of the competition.
Schalke's 1-1 draw against Montepellier combined with Arsenal's 2-1 defeat by Olympiakos Piraeus assured the German squad of first place in Group B.
The Gunners grabbed the other Group B slot in the knockout stage.
Malaga, a newcomer to the Champions League play, started Tuesday's match against Anderlecht with first place in Group C sewn up.
The hard-charging Spanish side was forced to settled for a 2-2 draw.
AC Milan, which was in no danger of losing its ticket to the knockout phase, lost 1-0 to Zenit St. Petersburg in the other Group C clash. EFE