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. Tottenham remain in the hunt, however, after Kane's late brace secured a 2-1 win over PSV Eindhoven.

Liverpool were strong favourites away to Red Star in Serbia, but Jurgen Klopp's team were poor in a 2-0 defeat to the 1991 European Cup winners. Milan Pavkov scored twice in seven first-half minutes, heading in the opener and then beating Alisson with a powerful strike from range, to the delight of a huge home support.

"The boys are very disappointed, I'm very disappointed and we have to do better. We have to do better because we can do better, but tonight it is too late," said Liverpool boss Jurgen Klopp.

"The atmosphere, noise-wise, was not a problem for us, but after the second goal they could smell it

"We made it too easy for them. They deserved it with the passion they showed. We lost our mojo in the game, not in general. We have to make sure it doesn't happen again."

The defeat exposes the Anfield club to the threat of an early elimination in Group C, with Napoli coming from behind to draw 1-1 at home to PSG  in the night's other game.

Kylian Mbappe set up Juan Bernat to put Paris ahead just before the break, but Lorenzo Insigne beat Gianluigi Buffon from the penalty spot in the second half as these sides played out a draw for the second time in a fortnight.

"This is a difficult group but we saw with Liverpool losing that everything is possible," said PSG's Julian Draxler. "A draw in Naples is not bad and we still have our fate in our own hands."

Liverpool and Napoli are locked on six points from four games, with PSG one behind and Red Star another point adrift. Liverpool travel to the French capital in their next game.

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 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.

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.