Chelsea, PSG through to last 16 as Juventus crash out

Juventus were knocked out of the UEFA Champions League in the group stage for the first time in nine years on Tuesday but Chelsea, Paris Saint-Germain, Benfica and Borussia Dortmund all secured qualification for the knockout stage with one group game to spare.

A 4-3 defeat away to Benfica in Portugal sealed the fate of a Juventus side who have been in decline in Europe for several seasons and have now lost four of their five matches in Group H.

Having already won when the sides met in Italy, Benfica went ahead in Lisbon when Antonio Silva headed in an Enzo Fernandez cross.

Moise Kean quickly equalised for Juve with a goal that was confirmed following a VAR review, but Joao Mario restored Benfica’s lead from the penalty spot and then set up Rafa Silva to make it 3-1 before half-time with a superb backheel flick.

The same player then got Benfica’s fourth early in the second half, and a Juventus fightback that produced goals by Arkadiusz Milik and Weston McKennie came too late.

Juventus had been knocked out in the last 16 in each of the last three seasons but they have not been eliminated from the Champions League in the group stage since 2013/14.

“I am angry and sad because we are out of the Champions League, but we must think about the league now,” said Juve coach Massimiliano Allegri, whose team are eighth in Serie A.

Benfica are joined in qualifying from Group H by PSG, with the 2020 Champions League runners-up through after crushing Israel’s Maccabi Haifa 7-2 at the Parc des Princes.

Lionel Messi and Kylian Mbappe both turned on the style, each scoring twice, while Neymar netted once and forced an own goal from Sean Goldberg.

Carlos Soler completed the scoring for PSG as they equalled their own record for goals scored in a single European game.

Abdoulaye Seck scored twice for Maccabi Haifa, and they could still finish third above Juventus.

Earlier, two-time Champions League winners Chelsea clinched their place in the last 16 as Group E winners, completing an impressive turnaround after they lost their first game to Dinamo Zagreb in September.

Graham Potter’s side won 2-1 away to Red Bull Salzburg, with a stunning Kai Havertz strike 26 minutes from time proving the difference between the teams after Junior Adamu cancelled out Mateo Kovacic’s opener for the Blues.

Victory extended Chelsea’s unbeaten run under Potter to nine games.

“That was a fantastic performance from the players,” said Potter.

“I’m delighted to go through with a game to spare considering where we started the competition.”

AC Milan are best-placed to go through with Chelsea after the Serie A champions won 4-0 in Zagreb, with Matteo Gabbia heading in the opener and Rafael Leao doubling their lead before Olivier Giroud netted a penalty and a Robert Ljubicic own goal completed the scoring.

Milan are now a point clear of Salzburg with the teams meeting at San Siro next week to decide which one progresses.

Dortmund are into the last 16 after getting the point they needed in a 0-0 draw at home to a Manchester City side who had already qualified.

City required just a point to secure top spot in Group G and they got it despite taking Erling Haaland off at half-time against his former club.

In fact, Pep Guardiola’s side could have got all three points but Riyad Mahrez had a second-half penalty saved by Gregor Kobel.

Sevilla will therefore drop into the Europa League despite beating FC Copenhagen 3-0 earlier on Tuesday with second-half goals by Youssef En-Nesyri, Isco and Gonzalo Montiel.

David Khocholava was sent off at the end for Copenhagen, who have still not scored a goal in the group.

Meanwhile, RB Leipzig inflicted a first defeat of the season on reigning European champions Real Madrid as they took a big step towards joining the Spaniards in qualifying from Group F.

Joskpo Gvardiol and Christopher Nkunku scored to have Leipzig two goals ahead before Vinicius Junior pulled one back. Timo Werner got Leipzig’s third with Rodrygo converting a late penalty for Real as it ended 3-2.

In Scotland, a stunning Mykhailo Mudryk goal gave Shakhtar Donetsk a 1-1 draw away to Celtic, for whom Giorgos Giakoumakis had opened the scoring.

While Celtic are out, Leipzig need just a draw at Shakhtar next week to advance.