Scotland put up a commendable fight against Germany in their Euro qualifier at Hampden Park but the 3-2 defeat leaves them battling for a play-off spot at best.
Gordon Strachan’s side went into the interval level after coming from behind twice with a Mats Hummels own goal and James McArthur strike cancelling out a Thomas Muller double.
But Ilkay Gundogan’s 54th-minute strike proved to be the winner for the world champions.
And with two Group D fixtures left for the Scots – second-place Poland and home and minnows Gibraltar away – they remain in fourth place, four points behind Republic of Ireland and six behind Poland.
It means Scotland cannot finish in the top two automatic qualifying places.
As expected Strachan freshened his side up for what was a big night in Glasgow.
Grant Hanley came back into central defence with Charlie Mulgrew moving to left-back at the expense of Andrew Robertson.
McArthur and James Forrest replaced Ikechi Anya and Steven Naismith, both of whom were on the bench.
The Germans showed just one change with Gundogan in for Karim Bellarabi.
Amid the usual pre-match preamble, Sir Alex Ferguson greeted the players to mark the 30th anniversary of the passing of Jock Stein, accompanied by the legendary boss’ son, George Stein.
Germany had shown in their home 3-1 win over Poland on Friday that they were getting back to their best and they looked comfortable in the early stages and in control when Muller, who scored twice in the 2-1 win over the Scots a year ago in the section opener, made his mark again, albeit with some fortune.
The Bayern Munich forward strolled all too easily into the danger area and when he sent his shot towards goal it took a nick off Martin’s foot and sped past David Marshall.
Scotland drew level in the 28th minute with some good fortune of their own. After defender Can was penalised for holding Mulgrew at the edge of the box on the left-hand side – it may well have been inside – Maloney fired in the free-kick. An unusually hapless Neuer could only push the ball on to the chest of Hummels and into the net.
Hampden came alive for the first time but it was soon deflated again when Marshall could only parry Can’s angled shot out to Muller whose header hit the post and went over the line as Mulgrew tried to clear.
Germany’s World Cup final hero Mario Gotze had the ball in the Scotland net in the 39th minute but was ruled offside, to much Tartan relief which turned to joy two minutes from the interval when McArthur guided a shot from 16 yards high past Neuer, after a corner had been cleared to his feet.
Five minutes after the restart Gotze had the ball in the net again, this time by getting his head to a cross from skipper Bastian Schweinsteiger, but again the flag was up.
However, the third German goal was only four minutes away and it came when the unmarked Gundogan steered Muller’s cut-back in off the post from 12 yards.
Maloney was replaced by Anya on the hour-mark, moments before Marshall had to parry a powerful Schweinsteiger drive away with Martin completing the clearance.
In the 66th minute Scotland defender Alan Hutton picked up a Steven Fletcher pass but just missed the target with his shot on the slide from eight yards.
Marshall had to deal with Gundogan’s powerful right-footed shot from the edge of the box before Gotze fired over from inside the box as the world champions remained too big, too strong and too skilful in the final stages.