Champions League holders Real Madrid suffered one of their worst European, losing 3-1 to Tottenham Hotspur at Wembley to put the London football club through to the last 16.
The sides went into the match as joint leaders of Group H but Tottenham were far superior as they ended Madrid's 30-match unbeaten run in Champions League group games in stunning fashion with Cristiano Ronaldo scoring a consolation goal for the visitors late in the match.
There was little for Cristiano Ronaldo and Real Madrid to celebrate at Wembley. Photo: Photosport
Sergio Aguero has become Manchester City's all-time leading scorer after netting the team's third goal in its 4-2 win against Napoli.
The Argentina striker moved onto 178 goals for City - one clear of Eric Brook, who scored 177 goals in 453 appearances from 1928-1940.
Aguero has scored his tally of goals in 264 games for City since joining from Atletico Madrid in 2011.
Sergio Aguero. Photo: Photosport
Liverpool cut loose after halftime to beat Maribor 3-0 and take a one-point lead in Group E and can now secure a top-two finish and a place in the knockout stage by beating Sevilla later this month.
Sevilla beat Spartak Moscow 2-1 in the other group game.
Besiktas moved a step closer to the knockout stages of the Champions League and pushed Monaco nearer the exit after the sides drew 1-1.
In other games Porto beat RB Leipzig 3-1 and Shakhat Donetsk were also 3-1 winners over Feyenoord.