Barcelona was eliminated from the Champions League on Wednesday even before enduring yet another 3-0 beating by Bayern Munich.
Atletico Madrid also went out following an extraordinary sequence around a penalty awarded by video review after the final whistle of its 2-2 draw with Bayer Leverkusen.
Atletico’s spot kick was saved before a frantic scramble in the goalmouth still could not bring the winning goal the Spanish club needed to prevent Porto advancing thanks to its 4-0 win earlier at group leader Club Brugge.
Canadian international Stephen Eustaquio scored as Porto punished Club Brugge’s defensive mistakes to hand the Belgian champion its first defeat in the Champions League this season and reach the knockout stage.
The 25-year-old Canadian midfielder made it 3-0 in the 60th minute, knocking home his own rebound after he was found unmarked by Porto striker Medhi Taremi.
It was his first Champions League goal.
Tajon Buchanan started for Brugge with fellow Canadian Cyle Larin on the bench.
Porto avenged its 4-0 home loss when the teams first met in Group B last month and advanced to the round of 16 after Atletico was held 2-2 by Leverkusen.
With one match left to play in the group phase, Porto moved one point behind group leader Brugge, which had already secured advancement before kickoff. Atletico stood third, five points off the pace, with Leverkusen lagging one point further back.
Brugge had not conceded a single goal in its four previous matches.
Two Spanish powers who were part of the failed Super League launch last year will now miss out on the round of 16 of Europe’s top competition.
Liverpool’s passage into the knockout stage with a game to spare was relatively calm in a 3-0 win at Ajax to join leader Napoli in advancing from free-scoring Group A, which has had 44 goals in 10 games.
In more stoppage-time drama with video review, Tottenham thought it had won Group D when Harry Kane shot the ball into Sporting Lisbon’s net with seconds left in a game tied at 1-1.
A long VAR check ruled Kane had been offside, a furious Tottenham coach Antonio Conte was shown a red card, and the most finely balanced group goes to the final round next week with all four teams having a chance to advance.
Group leader Tottenham plays at last-placed Marseille next Tuesday while Eintracht Frankfurt – which beat Marseille 2-1 on Wednesday – goes to Sporting.
The meeting between heavyweights in Barcelona was rendered meaningless before kickoff, when the five-time European champion’s hopes of advancing were ended by Inter Milan’s 4-0 win over Viktoria Plze in one of the early games.
Barcelona needed Inter to drop points and then still had to beat Bayern, which also beat the Spanish team 3-0 in two group meetings last season and won 2-0 at home in September.
The outcome was clear after Sadio Mane scored in the 10th minute. Eric Maxim Choupo-Moting doubled the lead before halftime and Benjamin Pavard added a third in stoppage time.
Barcelona, even after signing former Bayern star Robert Lewandowski, has now fallen short of the round of 16 in back-to-back seasons since Lionel Messi left in August 2021 for Paris Saint-Germain.
Bayern and Napoli are the only teams with five straight wins in this group stage, and the Italian team’s 3-0 win against Rangers ran its goal tally to 20.