Manchester United gave up a two-goal lead in a breathless 4-3 Champions League loss to FC Copenhagen on Wednesday that turned after Marcus Rashford was shown a controversial red card following a brace by young United striker Rasmus Hojlund.
The loss was a calamitous setback in United's hopes for last-16 qualification with Erik ten Hag's side fourth in Group A on three points with two group games still to play. Copenhagen are one point better off in second place.
Bayern Munich top scorer Harry Kane struck twice in seven minutes late in the game to guide his team to a 2-1 victory over Galatasaray and secure a spot knockout stage as group winners with two games to spare.
The England captain, who had scored a hat-trick against Borussia Dortmund in the Bundesliga on Saturday, headed in a Joshua Kimmich free kick in the 80th minute and then tapped in his second six minutes later to make sure of a top two finish.
Brahim Diaz, Vinicius Jr and Rodrygo scored as Real Madrid cruised into the last 16 of the Champions League with two group games remaining after a 3-0 victory over Portuguese side Braga
Real manager Carlo Ancelotti rested several regular starters, including top scorer Jude Bellingham with a shoulder injury, but the 14-times champions maintained their 100 per cent record to lead Group C with 12 points from four games.
They could secure top spot with a point at home in their next game against Napoli.
Arsenal returned to winning ways with a routine 2-0 defeat of Sevilla to take a big step towards qualification for the Champions League knockout rounds on Wednesday.
Successive defeats in the League Cup and Premier League had halted Arsenal's momentum but goals by Leandro Trossard and Bukayo Saka cemented their place as leaders of Group B.
Trossard tapped home in the 29th minute to put Mikel Arteta's side in front and Saka underlined Arsenal's superiority with a superb effort midway through the second half.
A late penalty by Lautaro Martinez helped Inter Milan book their spot in the Champions League last 16 with a 1-0 win at Salzburg dashing the Austrian champions' knockout stage hopes with two games remaining.
Substitute Martinez sealed the win for Inter from the spot five minutes from fulltime after Simone Inzaghi's men were awarded a penalty for a handball.
Inter are second in Group D on 10 points, level with leaders Real Sociedad who earned a comfortable 3-1 win in the other group fixture earlier on Wednesday and also secured a top-two finish with Inter's victory.