Manchester City and Arsenal have both been knocked out of the UEFA Champions League at the quarter-final stage after losing to Real Madrid and Bayern Munich respectively.
Holders City were beaten 4-3 on penalties at Etihad Stadium, coming from 1-0 down on the night to draw 4-4 on aggregate, as their hopes of a second successive treble were ended.
Meanwhile, Arsenal lost 3-2 on aggregate, with Bayern earning a 1-0 win thanks to a 63rd-minute header from Joshua Kimmich to book the Germans a place in the last four against Real.
The results mean there will be no English club in the semi-finals for the first time since 2020, and only the second time since 2017.
It also harms the Premier League's hopes of receiving an extra Champions League spot for 2024/25.
How Man City's match unfolded
Following a thrilling 3-3 draw in the first leg in Madrid, Real, who have won the Champions League a record 14 times, took a 12th-minute lead through Rodrygo, but it was City who dominated much of the match thereafter.
They struggled to find a breakthrough until the 76th minute, when Kevin De Bruyne finished from close range to take the match into extra-time.
After a goalless extra period, penalties were required. Ederson saved from Luka Modric with Real's first spot-kick, but Bernardo Silva and Mateo Kovacic also saw their efforts from 12 yards saved.
The decisive penalty came from former Chelsea defender Antonio Rudiger, who set up a meeting with Bayern in the semis.
Next up for Man City is a FA Cup semi-final with Chelsea at Wembley Stadium on Saturday, kicking off at 17:15 BST.
How Arsenal's match unfolded
After a 2-2 draw at Emirates Stadium last week, there were few clear-cut chances in the first half at Allianz Arena, but Arsenal 'keeper David Raya did have to be alert to keep out a long-range effort from Jamal Musiala.
Bayern started the second half quickly and struck the woodwork twice in quick succession, first through Leon Goretzka's header and then Raphael Guerreiro's follow-up .
The hosts stepped up the pressure and were rewarded with the only goal, as Kimmich powered in a header from Guerreiro's cross.
Arsenal were unable to find a response, missing out on their first Champions League semi-final appearance since 2009.
Mikel Arteta will have to galvanise his side, who are winless in three matches in all competitions, for their next fixture, a trip to Wolverhampton Wanderers in the Premier League on Saturday at 19:30 BST.