Barcelona secured their place in the Champions League knockout stage on Tuesday with a 1-1 draw away to Inter Milan, as Harry Kane revived Tottenham Hotspur’s hopes but Liverpool slumped to a shock defeat.

Last year’s runners-up were beaten by Red Star Belgrade, although the biggest losers on the night were Thierry Henry’s Monaco, who were eliminated following a resounding loss to Club Brugge.

Lionel Messi was still missing for Barcelona at the San Siro, and it was substitute Malcom who came off the bench to give the Spanish champions a late lead.

But Inter hit back to earn a point thanks to Mauro Icardi’s 87th-minute leveller, keeping the three-time former winners on course to join Barcelona in qualifying for the last 16 from Group B.

Meanwhile, Atletico Madrid gained revenge for a 4-0 defeat away to Borussia Dortmund last month as Diego Simeone’s side defeated the Germans 2-0 in Spain, Saul Niguez and Antoine Griezmann scoring the goals.

The two favourites in Group A are not guaranteed a path to the last 16 yet, however, after Club Brugge claimed a stunning 4-0 win at Monaco.

The Belgians had not won a Champions League match since 2005, but they were 3-0 up midway through the first half at the Stade Louis II. Hans Vanaken scored twice, including a penalty, and the Brazilian Wesley belted in the third before Ruud Vormer sealed the win.

‘Worrying’ for Henry

Semi-finalists in 2017, Monaco are now eliminated. It was a dreadful display from a side who have not won in 15 games, including five matches under Henry.

This result also came on the day the club’s Russian billionaire owner Dmitry Rybolovlev was arrested in a corruption investigation.

“We started well, but once we fell behind we stopped playing and that’s a little bit worrying,” said Henry of his team’s performance.

Porto are on the brink of qualification from Group D after a 4-1 win at home to Lokomotiv Moscow. They lead the section by two points from Schalke, who defeated Galatasaray 2-0 in Gelsenkirchen.