Agony and heartache - Wales' history of qualifying woes

Wales' World Cup dream is over after defeat in the play-off semi-final on penalties against Bosnia-Herzegovina in Cardiff.

Although Wales have qualified for three major finals in the past decade, their history is littered with a number of near misses and heartache.

BBC Sport Wales looks at Wales' previous qualification disappointments.

Wales had beaten group rivals Czechoslovakia 3-0 in Wrexham and a win over Scotland would have taken Mike Smith's men within touching distance of qualifying for the World Cup finals in Argentina.

Scotland had already lost 2-0 in Prague, and so Wales sensed their opportunity - even though the home match would be played on foreign soil.

Forced to play away from Ninian Park due to crowd trouble, the Football Association of Wales (FAW) decided to stage the crucial match at Liverpool's Anfield rather than Wrexham in order to secure more money from a larger crowd.

The game's turning point came in the 78th minute when Scotland striker Joe Jordan rose with Wales defender David Jones to challenge for Asa Hartford's long throw into the Welsh box.

To the astonishment of the Welsh fans and players, French referee Robert Wurtz awarded a penalty, even though TV replays clearly showed it was Jordan's and not Jones' hand deliberately flicking the ball towards goal.

Don Masson coolly slotted the penalty past Dai Davies, and with Kenny Dalglish adding a second goal 10 minutes later, the Wales dream was over.

Mike England's Wales were unbeaten in their first five games of the World Cup qualifying campaign but after defeat in Czechoslovakia a home draw against Iceland proved costly.

Wales were leading 1-0 at the Vetch Field in Swansea when the floodlights failed before the interval, and following a lengthy delay, Iceland twice came from behind to draw 2-2.

England's side lost 3-0 to the Soviet Union a month later and Wales' faint hopes were finally extinguished when the Soviets drew 1-1 with Czechoslovakia, who finished above Wales on goal difference and qualified for Spain 1982.

On the verge of getting through to the 1984 European Championship finals in France, Wales were denied by a late Yugoslavia equaliser in their final group game in Cardiff.

"We scored the goal that mattered and we were nine minutes away from glory," manager Mike England reflected post-match.

With their fate out of their hands, Wales could only look on as Yugoslavia finished a point clear at the top of the group thanks to an injury-time winning goal in the final group match against Bulgaria.

"I really thought we were going to France. My feelings when the injury time goal went in are impossible to describe. I just felt sick," added England.

After losing their opening two games away to Iceland and Spain, Wales got themselves back into the World Cup qualification mix with two impressive wins – away to Scotland and a 3-0 home win over Spain in which Mark Hughes scored a spectacular scissor kick.

It set up a huge return match with Scotland in the final group game at Ninian Park in September 1985 – Wales had to win the game while a draw was enough for Scotland.

Manchester United's Hughes gave Wales the lead in the first half but as was the case in 1977, Scotland benefited from a controversial handball decision.

David Phillips was adjudged to have handled the ball and substitute Davie Cooper squeezed his penalty past Neville Southall to earn the Scots the draw they needed.

Wales' disappointment of missing out on Mexico was put into perspective with the death of Scotland manager Jock Stein, who had collapsed at the end of a frenetic game.

Wales had looked on course to qualify for the finals in West Germany after an impressive 1-0 win over Denmark in Cardiff in September 1987 which maintained their unbeaten record in the group.

But Wales' hopes unravelled in their two remaining away games – against Denmark and Czechoslovakia.

Despite a narrow 1-0 defeat in Copenhagen, Wales knew a win in Czechoslovakia in their final game would ensure top spot and qualification for the finals.

But Ian Rush missed a number of chances and it proved costly as the home side scored in either half to secure victory as Wales once again suffered heartbreak at the final hurdle.

"The disappointment of losing – you could see it in their faces," said England, reflecting on the defeat in Prague.

"Some were crying, some were sitting in the corner heads bowed and I felt for them because I'd been there myself and I knew how they felt."

Czechoslovakia would prove to be England's final game after seven years at the helm – paying the price for missing out four times on qualification.

Despite a 5-1 defeat in their opening qualifier in Romania, Wales got themselves back into contention during the campaign which saw the emergence of Ryan Giggs, who scored in a 2-0 win over Belgium.

It would all come down to the final round of fixtures.

Romania were the opponents at a packed National Ground in Cardiff. Wales had to win by two goals to be certain of qualification, but any kind of victory would be enough if results went their way.

Gheorghe Hagi gave the visitors a first half lead but in the second half Dean Saunders equalised for Wales, who were then awarded a penalty when Gary Speed was upended in the penalty area.

Up stepped Paul Bodin to take the penalty but his spot kick struck the crossbar and late in the game Florin Raducioiu added a second for Romania and Wales' World Cup dreams were over.

"We're still the nearly men," Wales manager Terry Yorath said following the game. "I'm afraid that's the tag we're going to have again."

The defeat was put in perspective when Welsh fan John Hill died after being hit by a marine distress flare.

The game would be Yorath's final game in charge, with the FAW deciding not to offer him a new contract.

Under Mark Hughes, Wales had a storming start to their Euro 2004 qualifying campaign with four consecutive wins – including a famous 2-1 win over Italy in Cardiff, in which current boss Craig Bellamy scored.

But the second half of the campaign saw Wales fail to win any of the remaining four games, missing out on automatic qualification and limping over the line to secure a play-off spot.

They secured a goalless draw against Russia in the first leg in Moscow but Vadim Evseev's goal in the second leg secured Russia's win and a passage to the finals in Portugal.

Having enjoyed great success at Euro 2016 where they reached the semi-finals, Wales went on to qualify for Euro 2020 and the 2022 World Cup.

Wales, led by boss Rob Page, were looking to qualify for their third successive major tournament as they began their Euro 2024 campaign.

A mixed campaign which included a win against Croatia and a loss at home to Armenia meant Wales had to rely on the play-offs.

Page's side eased past Finland 4-1 in the semi-final to set up a play-off final tie with Poland in Cardiff.

It finished goalless between the two sides after 90 minutes and extra time, so penalties would decide which side would reach the 2024 tournament in Germany.

Ben Davies, Kieffer Moore, Harry Wilson and Neco Williams all scored for Wales but Dan James saw his penalty saved and Poland progressed.