Scotland missed out on Nations League promotion after falling to a 1-0 defeat in Israel.
Manor Solomon scored on the counter-attack a minute before half-time to allow the Czech Republic to leapfrog Scotland and take top spot in Group B2 following their win over Slovakia.
Scotland had enjoyed a dangerous spell before the goal and looked threatening immediately after the break. But some attacking-minded substitutions failed to transmit into chances as Israel held on.
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Steve Clarke’s side had come into November four points clear at the top but consecutive defeats cost them.
Winning the group would have put Scotland in the running for two World Cup play-off places, if needed.
Promotion to the top tier would also have enhanced chances of making Euro 2024.
Clarke picked the same team that started in Scotland’s Euro 2020 play-off win over Serbia last week.
Ryan Christie hit a free-kick into the wall after being fouled in the act of shooting but there was little else in the way of threats at either end in the opening 15 minutes.
Israel got the first shot on target when Sun Menachem got in behind Stephen O’Donnell. He met a deep cross but shot straight at David Marshall from a tight angle.
Scotland began to exert some pressure and created two good chances around the half-hour mark.
Kieran Tierney played a penetrating ball forward and sharp passes from John McGinn and Ryan Jack set up O’Donnell, but the wing-back drove the ball across the face of goal.
Scott McTominay soon whipped in an excellent cross but Ofir Marciano pushed over a backward header from his former Hibernian team-mate McGinn.
Christie then under-hit a lay-off to McGinn after a long ball put Israel in trouble and Scotland had a let-off when Eran Zahavi took a heavy touch as he checked to shoot.
Callum McGregor’s cutback evaded a Scotland shirt before Lyndon Dykes had a header saved, but the visitors were soon caught on the breakaway.
The skilful Solomon was left one-on-one with McTominay, turned him on the outside and fired inside the far post.
Zahavi and Shon Weissman came close for Israel in the opening stages of the second half but Scotland were attacking with purpose. McGinn had two shots diverted for corners and Declan Gallagher headed over from seven yards after getting a clear run at Christie’s delivery.
Christie then brilliantly sent O’Donnell away on a break but Marciano got down well to save the Motherwell man’s powerful strike.
Clarke made a double switch on the hour mark, sending on strikers Leigh Griffiths and Oli McBurnie for McGinn and Dykes.
But, as Israel sat deeper, the openings dried up for Scotland and Clarke made two more changes in the 73rd minute. Scott McKenna replaced Gallagher in a straight swap and winger Oliver Burke came on for O’Donnell to add more attacking threat.
McBurnie soon did well to get a diving header on target from McTominay’s cross but Marciano got down reasonably comfortably.
Burke quickly got some decent crosses in before Marshall kept Scotland’s hopes alive by blocking a shot from Israel substitute Eyal Golasa after a counter-attack.
Chances eventually arrived in the final three minutes but the frustration continued for Scotland.
McKenna headed Andy Robertson’s cross just wide before a long throw fell invitingly for Griffiths but the striker could not get hold of his half-volley and the ball trundled into Marciano’s hands.
If there was any doubt it was not Scotland’s night then it was confirmed when Israel right-back Eli Dasa handled in his box and saw Marciano stop the ball going straight in.
Marciano then parried a Griffiths free-kick six minutes into stoppage-time.
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Aleksandar Mitrovic missed Serbia’s all-important penalty to send Scotland through the European Championship finals.
Scotland, of course, did it the hard way as they reached their first major tournament since 1998 after a 1-1 draw.
Ryan Christie’s strike appeared to have sent Steve Clarke’s dominant side to their first major tournament since 1998 but Serbia scored with their first effort on target in the 90th minute.
However, the blow proved to be fleeting as Marshall saved from Aleksandar Mitrovic in the 10th penalty of the shoot-out.
Christie gave Scotland a deserved 52nd-minute lead with an excellent strike from outside the box and Steve Clarke’s side had chances to give themselves an extra cushion.
They would regret not getting a second goal, despite looking comfortable for the vast majority of normal time.
Marshall was rarely troubled, the Scotland defence were resolute when they needed to be, the midfield composed and confident and Christie, John McGinn and Lyndon Dykes gave the home defence serious problems.
But Serbia put Scotland under some late aerial pressure and Luka Jovic headed home unchallenged following a corner 20 seconds before the 90-minute mark.
However, Scotland secured a 5-4 penalties triumph to set themselves up for two Hampden encounters against Croatia and Czech Republic and a Wembley clash with England at next summer’s delayed finals.
Never in doubt… #SRBSCO pic.twitter.com/4gvyHtVFHy
— Scotland National Team (@ScotlandNT) November 12, 2020
The signs were good coming into the clash in Red Star’s Rajko Mitic Stadium.
Scotland were eight matches unbeaten and had recorded four wins and three clean sheets on the trot.
Clarke went with the bulk of the team that had won three matches in October but Kieran Tierney and Christie returned, the latter for the injured Ryan Fraser, after the pair were instructed to self-isolate last month.
There was more encouragement from the early stages as Scotland dominated possession and territory in the opening 10 minutes, getting several crosses into the box without finding a blue shirt, before Christie drew a save from an ambitious free-kick.
Serbia were barely seen as an attacking force until coming close midway through the half. Aleksandar Mitrovic laid the ball back for Sasa Lukic who steered the ball a yard wide from the edge of the box.
Scotland came closer when Christie fed McGinn after a long ball, the latter’s shot gathered at the second attempt.
Scotland continued to threaten and skipper Andy Robertson spurned a glorious chance five minutes after the break after Lyndon Dykes had seen off three defenders to roll the ball into his path. The Liverpool player sliced his shot well over.
The Scots were ahead 90 seconds later. Callum McGregor intercepted and fed his Celtic team-mate, Christie, who swivelled and fired the ball in off the post from 22 yards.
Christie soon had a volley saved following a Dykes head-on and Scotland remained in control.
Serbia had to step up a gear and did so in the final 20 minutes. Headers from Sergej Milinkovic-Savic and Mitrovic were not far wide but Scotland were still creating chances.
McGregor saw a long-range effort swerve just wide and Christie came close after running on to a long ball.
The home pressure increased and Jovic headed wide from a good chance but Scotland looked to be riding it out until the substitute evaded marker Scott McTominay amid a crowd of bodies to head home unchallenged from Filip Mladenovic’s corner.
Clarke had taken off his most advanced three players in the final seven minutes of normal time with Oli McBurnie, Callum Paterson and Kenny McLean now finding themselves leading the charge after being brought on to help shore up a lead.
Stephen O’Donnell and Ryan Jack came close from long range in the opening moments but Scotland were soon under pressure again and Marshall produced a brilliant fingertips save to divert Nemanja Gudelj’s long-range effort away from the top corner.
Scotland had lost their attacking rhythm and Clarke threw on Leigh Griffiths in the 117th minute for his first cap in more than two years.
Griffiths’ first involvement was to fire home the opening penalty of the shoot-out. McGregor, McTominay, McBurnie and McLean also netted before Marshall denied Mitrovic.
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