Ryan Fraser won his 11th cap for Scotland in their 4-0 defeat by Russia in a Euro 2020 qualifier in the Luzhniki Stadium in Moscow last night.
The Scots conceded four times in 27 second-half minutes as their slender hopes of automatic qualification were finally extinguished.
Russia eased into a 2-0 lead thanks to goals from Artem Dzyuba and Magomed Ozdoev before Fraser was replaced by Ryan Christie in the 68th minute.
Dzyuba and Aleksandr Golovin added further goals to leave Scotland fifth in Group I and they can no longer finish in the top two although they could still qualify via the Nations League play-offs, which begin in March.
Nathan Ake was an unused substitute as the Netherlands claimed a dramatic 3-1 win over Northern Ireland in Rotterdam.
Josh Magennis headed Northern Ireland into a 75th-minute only for Memphis Depay to equalise five minutes later.
Luuk De Jong’s goal in the first minute of injury-time gave the hosts the lead before Depay slid the ball into the net for his second soon after.
The win saw the Dutch move top of Group C, ahead of Germany and Northern Ireland on goal difference.
Harry Wilson replaced Jonny Williams midway through the second half of Wales’ 1-1 draw with Slovakia in Trnava.
Wigan’s Kieffer Moore registered his first international goal to give Wales the lead in the 25th minute before Slovakia equalised through Juraj Kucka eight minutes into the second half.
Wilson came on for Williams in the 66th minute before the hosts were reduced to ten men when Norbert Gyomber was sent off for a second yellow card late on.
Wales remained fourth in Group E, behind Hungary who lost 3-0 to group leaders Croatia.
Gavin Kilkenny replaced skipper Jayson Molumby in the closing stages of Republic of Ireland’s 0-0 draw with Italy in a European Under-21 Championship qualifier in Dublin.
Troy Parrott received a second yellow card following a 64th-minute coming together with Italy striker Moise Kean who received a straight red card for his part in the incident.
Kilkenny, who featured in wins against Armenia and Sweden last month, won his third cap for the under-21s when he came off the bench five minutes from time in front of a sell-out at Shamrock Rovers’ Tallaght Stadium.
The Boys in Green remained top of Group One with ten points from four games.
Callum Wilson will be hoping to feature in England’s Euro 2020 qualifier against Czech Republic in Prague tonight.
Aaron Ramsdale, Lloyd Kelly and Sam Surridge are in the England under-21 squad for their friendly in Slovenia, while Ben Greenwood could debut for Republic of Ireland under-19s in their friendly with Denmark.