Cristiano Ronaldo faces the threat of missing the World Cup after his Portugal side were drawn against Italy whilst Scotland could face Wales for a place at Qatar after being drawn in the same path.
One of Italy or Portugal will not be at the World Cup next year after being drawn in the same path in the play-off draw.
The last two winners of the Euros have been drawn against North Macedonia and Turkey respectively in Path C.
but if they both win will square off in a winner takes all clash in Portugal, meaning Cristiano Ronaldo could fail to make it to a World Cup for the first time in his career.
He is aiming to appear in the competition for a fifth time, but could see his dreams dashed.
Portugal were beaten in their final group game by Serbia in Lisbon which forced them into the play-offs, rather than going through automatically as group winners.
Italy boss Roberto Mancini has already said: “It’s very difficult for us because North Macedonia is a good team, and if we win we have to play away…”
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Scotland and Wales could also square off after being drawn into Path A together.
The Scots, aiming to reach their first World Cup since 1998, will take on the Ukraine whilst Wales will face Austria.
Wales have only made the World Cup once, way back in the 1950s but are looking to build on steady momentum.
They have qualified for the last two Euros, making the semi-finals back in 2016, and will no doubt fancy themselves after the draw.
Their boss Robert Page said: “We have given ourselves a great opportunity. It was 1958 when we qualified from a play-off again.
“We have worked ever so hard to finish second in the group. Everything to play for.”
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Should they win they will enjoy home advantage against either Scotland or the Ukraine.
In Path B Russia will take on Poland and Sweden will tackle the Czech Republic. Russia were at the last World Cup by virtue of being hosts.
Either they or Robert Lewandowski’s Poland will be the team hosting the Path B final.
Sweden were edged out in their group campaign by Spain whilst the Czechs, who made it to the last eight of the Euros in the summer, came third in their group behind Belgium and Wales.
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