UEFA Champions League: Juventus Sink Manchester City, Manchester United Held

Last season's beaten finalists Juventus joined Paris Saint-Germain, Atletico Madrid and Benfica in clinching qualification for the last 16 of the Champions League with one round of group games to spare on Wednesday.

Mario Mandzukic turned in Alex Sandro's cross to give Juve a 1-0 win over Manchester City in Turin and ensure that the Italian champions joined City in qualifying from Group D.

City had already secured their progress before the game but the defeat leaves them two points behind Juventus with one match remaining and therefore staring at the prospect of finishing second in the group and facing a tougher last-16 draw.

"Hats off to the lads, they've gifted me qualification with a game to spare," said Juventus coach Massimiliano Allegri.

As it happened, Juve would have been through regardless of their result because Sevilla lost 4-2 to Borussia Moenchengladbach in Germany.

Lars Stindl scored twice for Gladbach either side of a brilliant Fabian Johnson goal and a Raffael strike with Vitolo and Ever Banega, from a penalty, replying for Sevilla.

Sevilla, Europa League winners in each of the last two seasons, now must beat Juve in their final game and hope Gladbach don't defeat City just to claim the consolation of dropping into the secondary competition.

Zlatan Ibrahimovic captained PSG as he returned to face Malmo, his hometown team and the club where his glittering career began, and he was among the scorers in a 5-0 romp that took the French champions through from Group A.

Adrien Rabiot and Angel Di Maria netted in the first half before Ibrahimovic finished past Johan Wiland early in the second period.

Markus Rosenberg missed a penalty for Malmo before Di Maria scored again and substitute Lucas curled in a free-kick to complete the rout.

"I lived a dream tonight, coming back. On top of that I scored one. I'm very happy," said Ibrahimovic.

However, Real Madrid, who had already qualified, secured top spot in the group with an entertaining 4-3 win away to Shakhtar Donetsk in Ukraine.

A Cristiano Ronaldo brace either side of a Luka Modric goal and a delightful Dani Carvajal chip had Madrid out of sight but Shakhtar set up a grandstand finale with three goals in the last 13 minutes.

Alex Teixeira scored two of them, the first a penalty, while Dentinho also scored, but Rafa Benitez's under-pressure side held on.

Shakhtar are out but have third place and a Europa League place in their hands.

Atletico and Benfica will meet in Lisbon in two weeks to decide who finishes top of Group C after both qualified for the next phase on Wednesday.

Atletico eased to a 2-0 win over Galatasaray at the Vicente Calderon with Antoine Griezmann scoring both from Gabi assists, while Benfica came from two goals down earlier in the day to draw 2-2 at Astana.

Ghanaian forward Patrick Twumasi put Astana ahead in Kazakhstan and Marin Anicic doubled their lead on 31 minutes.

However, Mexican forward Raul Jimenez pulled one back before half-time and then levelled the scores in the 72nd minute, and a draw against Atletico will see Benfica win the group.

In contrast, there is still all to play for in Group B with Manchester United playing out a disappointing 0-0 draw against PSV Eindhoven at Old Trafford.

On a night when Old Trafford marked 10 years since the death of United legend George Best, the hosts knew a win would take them through but created few genuine chances.

"The result is disappointing because I have still the feeling that we could have finished this game several times," said United manager Louis van Gaal.

Wolfsburg are now top of the group after Andre Schuerrle came off the bench to provoke an Igor Akinfeev own goal and score one of his own in a 2-0 defeat of CSKA Moscow in Russia.

As a result, United now need to win their final game at Wolfsburg on December 8 to be certain of a place in the knockout phase, with PSV also still in contention.

On Tuesday, holders Barcelona qualified for the knockout stage with a 6-1 win over Roma, while Bayern Munich joined them by beating Olympiakos 4-0 and Zenit St Petersburg, who had already qualified, made it five wins in a row by beating Valencia 2-0 in Group H.