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Cristiano Ronaldo scored two minutes from time as Scotland fell to a 2-1 defeat to Portugal in the Nations League.
The 39-year-old tapped in from close range from Nuno Mendes’ whipped cross for his 901st career goal as Steve Clarke’s side’s poor run of results extended to one win in 14 games.
Earlier the visitors had taken a surprise lead in Lisbon when Scott McTominay peeled away at the back post to convert Kenny McLean’s cross, before Angus Gunn’s error in the Scotland goal allowed Bruno Fernandes to level with a tame long-range effort.
In the same group, Luka Modric scored his 27th international goal on his 180th cap as Croatia beat Poland 1-0 in Osijek to hand his side their first points of their Nations League campaign.
Northern Ireland went down to a 1-0 loss in Plovdiv against Bulgaria, a mistake by goalkeeper Bailey Peacock-Farrell gifting the home side the winning goal in the second half.
A poor pass out intended for Daniel Ballard was intercepted by Bulgaria’s Aleksandar Kolev who squared it for Kiril Despodov to tap in at the far post and condemn Michael O’Neill’s side to defeat.
Belarus were 1-0 winners away in Luxembourg thanks to Valery Gromyko’s second-half goal.
Elsewhere, Spain were 4-1 winners away in Switzerland despite playing for more than 70 minutes with 10 men, with Fabian Ruiz scoring twice for the European champions.
The Paris St Germain midfielder netted in the 13th minute, turning the ball home after Nico Williams’ shot was saved, to double his side’s lead after Joselu’s early header had broken the deadlock in Geneva.
Robin Le Normand was then sent off before Zeki Amdouni pulled one back for the hosts before half-time.
Ruiz scored his second in the 77th minute, then Ferran Torres also netted late on to complete the rout.
Denmark maintained their perfect start to the competition thanks to a goal in each half from midfielder Albert Gronbaek and Yussuf Poulsen as they eased to a 2-0 win at home to Serbia.
Newcastle’s Alexander Isak scored as Sweden ran out 3-0 winners at home to 10-man Estonia, with Viktor Gyokeres scoring twice, whilst Slovakia defeated Azerbaijan 2-0.
Gibraltar were denied victory over Liechtenstein by a goal scored in 14th minute of stoppage time, Nicolas Hasler’s penalty snatching a 2-2 draw after Manchester United’s James Scanlon’s 97th-minute goal looked to have won it.
