Wales' hopes of Euro 2024 qualification were seriously damaged by a humiliating 4-2 defeat to Armenia in Cardiff.
Lucas Zelarayan and Grant-Leon Ranos both scored twice as Armenia - ranked 97 in the world and 71 places lower than Wales - secured one of the greatest victories in their football history.
Daniel James had given Wales an early opener and Harry Wilson cut the deficit to 3-2 after Armenia had seized control, aided by some truly desperate home defending.
But Armenia responded in style and Welsh misery was completed by the dismissal of Kieffer Moore, who was adjudged to have committed foul play by Bulgarian referee Georgi Kabadov after tangling with goalkeeper Ognjen Chancharevich.
Moore will miss Monday's trip to Turkey that now takes on extra significance for Wales after this setback.
It was a sweet success for Armenia coach Olesksandr Petrakov, 12 months on after his Ukraine side were beaten in a World Cup play-off final in Cardiff.
Turkey helped their chances of beating Wales to qualification out of Group D after Irfan Kahveci’s 95th-minute goal earned a 3-2 win in Latvia, seconds after the hosts had equalised.
Elsewhere, Giorgos Masouras left the Republic of Ireland's qualification hopes hanging by a thread as they slumped to a 2-1 defeat in Greece.
Olympiacos midfielder Masouras scored the decisive goal in a victory for Gus Poyet's side which leaves them with maximum points from their opening two Group B fixtures and Ireland with none heading into Monday's home clash with Gibraltar.
Defender Nathan Collins had earlier cancelled out Tasos Bakasetas' 15th-minute penalty to give the visitors hope, but in truth Stephen Kenny's men, who had defender Matt Doherty dismissed in the dying seconds, were out-played for long periods at the OPAP Arena in Athens.
What a move, what a finish 👏🇦🇲
— Viaplay Sports UK (@ViaplaySportsUK) June 16, 2023
Disaster for Wales in Cardiff with Armenia leading by two now!#EURO2024 pic.twitter.com/gQqe14tnTt
Olivier Giroud and Kylian Mbappe were on target as France won 3-0 at Gibraltar to maintain their perfect start to qualifying in Ireland’s group.
Northern Ireland had a stoppage-time equaliser ruled out by VAR as a battling display went unrewarded in a 1-0 loss to Denmark.
Jonas Wind's goal early in the second half made the difference in Copenhagen as debutant Callum Marshall saw a dream goal ruled out for offside after a review which took almost five minutes.
The West Ham youngster flicked the ball in after Jonny Evans headed on a free-kick, but there was despair when referee Daniel Stefanski eventually signalled for offside after his colleague Tomasz Kwiatkowski took an age to review the footage.
Ukraine came from two goals down to win 3-2 in North Macedonia, who next travel to England after the Three Lions claimed a 4-0 win in Malta.