PSV Eindhoven became the first team to hold Arsenal scoreless this season, beating the Gunners 2-0 on Thursday to keep alive the fight for first place in their Europa League group.
Joey Veerman and substitute Luuk de Jong scored in the second half for PSV to hand Premier League leader Arsenal only its second loss of the season in all competitions and first in the Europa League.
De Jong set up Veerman to shoot past Aaron Ramsdale from inside the area in the 56th minute before heading in the second seven minutes later.
PSV forwards Cody Gakpo and Xavi Simons had a goal each disallowed due to offside in the first half.
Arsenal still leads Group A with 12 points, with Eindhoven second on 10 with one round remaining. Both teams have qualified for the next stage, but the group winners advance directly to the last 16, while teams qualifying second go through an extra playoff round.
Those in third place drop into the third-tier Europa Conference League.
Real Betis secured first place in Group C after a 1-0 victory at Ludogorets, with Nabil Fekir scoring the winner. The Spanish club has 13 points while Ludogorets is second, six points behind.
Fenerbahçe staged a late come back to salvage a 3-3 home draw against Rennes with both sides already qualified from Group B.
Amine Gouiri netted twice and Martin Terrier added one in the opening 30 minutes to put the visitors on course to win the group. The Turkish side replied with a goal from Enner Valencia still in the first half before substitutes Miha Zajc and Emre Mor scored in the 82nd and 88th, respectively. Both teams are on 11 points ahead of the final round of games.
Teddy Teuma and Lazare Amani scored in the first half to lead Belgian club Union SG to the round of 16 from Group D after a 2-0 victory at Malmö.
Union SG tops the group with 13 points with Bundesliga leader Union Berlin moving to second with nine points after a 1-0 home win over Braga, which is third on six.
Lazio came from a goal down to beat Midtjylland 2-1 to take a provisional three-point lead in the tightly contested Group F. Sergej Milinković-Savić and Pedro Rodríguez replied after an opening goal by Gustav Isaksen for the Danish side. All four teams in the group were on five points before the fifth round of matches. Sturm hosted Feyenoord later in the group’s other game.
PSV was punished earlier Thursday for fan disorder inside Arsenal’s stadium in their previous meeting, which Arsenal won 1-0.
UEFA banned PSV from selling tickets to its fans for the team’s game in Norway next week against Bodø/Glimt.
The Dutch club must also pay a fine of 40,000 euros ($40,000) and compensate Arsenal for damage to seats in the stadium last week.
EUROPA CONFERENCE LEAGUE
Fiorentina came from a goal down to beat İstanbul Başakşehir 2-1 and draw level with their Turkish opponent atop Group A with 10 points. Both teams mede it to the next round.
Villarreal’s perfect record came to an end after it was held 2-2 at home by Hapoel Beer-Sheva. But the Spanish club was already assured of qualifying in first place from Group C and avoiding the extra playoff round.
AZ Alkmaar had a five-point lead atop Group E after a 2-0 away win at Vaduz.
The kickoff of the Group D match between Czech side Slovácko and Cologne was initially delayed by 75 minutes due to heavy fog. But six minutes after the game started the fog again made it impossible to play. The match is scheduled to resume on Friday at 1 p.m. (1100 GMT).