Three Liverpool suffered a bruising Saturday of international action, with Andy Robertson, Alexander Isak and Giorgi Mamardashvili all beaten while playing for their respective countries.
Of the trio, it was Robertson and Scotland that endured the most distressing and chaotic night. The Scots traveled to Greece knowing it needed to keep pace with group leaders Denmark ahead of their meeting in Glasgow on Tuesday.
But Steve Clarke's side failed to impose itself on proceedings, with Greece dominating for long spells of the first half. Scotland found itself 3-0 down after 63 minutes, but rallied and nearly earned a valuable point.
Ex-Red Ben Gannon-Doak scored, before Robertson picked out Ryan Christie to head home in the 70th minute. That set up a dramatic conclusion in Piraeus, which was amplified by Anastasios Bakasetas' harsh red card.
Scotland pushed for an equalizer, but several outstanding saves from Greece keeper Odysseas Vlachodimos denied the Tartan Army.
The 3-2 defeat handed Denmark the initiative in the group, but to add to the drama, it suffered a shock slip-up against Belarus. A 2-2 draw means the Danes head into the final round of games a point ahead of Scotland.
The sides meet at Hampden Park on Tuesday in a winner-takes-all clash to secure a spot at next summer's World Cup. The loser will be forced to compete in March's play-offs.
Elsewhere, Isak made his return from injury as he played 28 minutes in Graham Potter's first game as Sweden head coach.
But there was no upturn in fortune, however, with the Scandinavians beaten 4-1 by Switzerland. Sweden knows it cannot qualify for the World Cup via the group stage, but could still be handed a spot in the play-off via the Nations League route, despite amassing just one point from its five group games.
Isak managed only 13 touches after his introduction and failed to have a shot. However, Arne Slot will no doubt be delighted to see his expensive summer acquisition play for the first time in nearly four weeks.
Mamardashvili was the final Liverpool player in action. He was on the receiving end of a brutal 4-0 loss against Spain, but did make an impressive first-half save to keep out Mikel Oyarzabal.
Despite the disappointment of the heavy defeat, it did not impact Georgia's chances of qualification to the World Cup, with a top-two finish already unachievable.