Man City well beaten in Madrid by Valverde hat-trick amid torrid first legs for English sides in Champions League
Kai Havertz's late penalty against former club Bayer Leverkusen rescued Arsenal a 1-1 draw in the first leg of their last-16 Champions League tie, while both Manchester City and Chelsea slipped to heavy defeats.
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Havertz, who spent 10 years at Leverkusen before joining Chelsea for £71million in 2020, converted an 89th-minute spot kick at the BayArena after Leverkusen midfielder Malik Tillman's challenge on Noni Madueke.
The Gunners, who finished top of the league phase after winning all eight of their matches, saw their 100 per cent record in this season's competition halted.
They fell behind in a Champions League tie for the first time in this campaign when Robert Andrich headed Leverkusen ahead early in the second half.
Arsenal had gone close to taking a first-half lead when Gabriel Martinelli's shot hit the crossbar.
Chelsea twice hit back to equalise against Paris St Germain at Parc des Princes before the holders struck three late goals to secure a commanding 5-2 first-leg lead.
Bradley Barcola's opener for PSG was cancelled out by Malo Gusto and after Ousmane Dembele gave the home side an interval lead, Enzo Fernandez levelled it up again for Chelsea shortly before the hour-mark.
PSG regained the lead through Vitinha and Chelsea thought they had equalised for a third time late on through Joao Pedro, but his effort was ruled out for offside.
Khvicha Kvaratskhelia then scored twice in eight minutes in the closing stages to give Luis Enrique's side a three-goal advantage and put them in firm control of the tie.
Real Madrid midfielder Federico Valverde struck a first-half hat-trick to leave City also facing an uphill struggle in next week's return leg after they lost 3-0 at the Bernabeu Stadium.
Valverde scored twice in seven minutes midway through the first period for Real, who were without injured duo Kylian Mbappe and Jude Bellingham, before he added a brilliant third three minutes before the interval.
City offered little attacking threat and it could have been worse in the second half when their goalkeeper Gianluigi Donnarumma saved Vinicius Junior's penalty.
In Wednesday night's other last-16 tie, Norwegian side Bodo/Glimt completed another memorable night by defeating Sporting 3-0 at home, making it five straight Champions League wins in their first season beyond the qualifying rounds.