West Ham and European competition are about as well-matched as Norwich City and Premier League consolidation.

David Moyes’s surprisingly successful campaign last season ensured the Hammers qualified for automatic European football for the first time since the dawn of the Premier League era, a timespan that has seen their ever-fluctuating fortunes mirror their sporadic and largely pitiful attempts to deliver regular European football to East London.

The following three exits since have seen the club disastrously fail at the final qualifying spot, each in equally frustrating contexts for their supporters, implying the club’s dreams repeatedly “fading and dying” emblem may not be such a myth. 

1999/2000: Intertoto Glory

Even a record-high fifth-place finish was not enough to guarantee automatic European football for Harry Redknapp’s side the previous season.

Due to only one viable automatic qualification spot, West Ham were facing three two-legged ties in the less-glamorous, now-defunct Intertoto Cup to earn a place in the UEFA Cup first round.

Four of the games were played before the new Premier League season started and after beating Finnish side FC Jokerit and SC Heerenveen, West Ham narrowly lost the home-leg of the final 1-0 to FC Metz.

They managed to win the return leg convincingly 3-1 at the Saint-Symphorien Stadium, a night that Harry Redknapp has since described as “his greatest night as West Ham’s manager”.

Whether the Intertoto trophy sits proudly aloft in West Ham’s roomy trophy cabinet, is unconfirmed.

For long-term club servant Steve Lomas, the trophy presentation did not extend to even a winner’s medal.

The Trophy was so small. It’s the only trophy I won in my career – that little egg sized cup…I think John Moncur might have kicked it across the changing room, so in West Ham’s trophy cabinet there might be a dent in it” said Steve Lomas in recent years.

Having qualified for the UEFA Cup First Round, light work was made of NK Osijek, overcoming the Croatian side 6-1 on aggregate.

However, their bubble was to be burst by a side from a country that would return to haunt the Hammers in years to come.

A disappointing 2-0 defeat in Romania to Steaua Bucharest – courtesy of two shocking examples from the East London School of Defending – was followed by a freakish 0-0 draw back at Upton Park that somehow remained goalless despite both sides peppering each other’s goals with long-range efforts in a remarkable display of agile goalkeeping that ended their European dreams.

Harry Redknapp left the club at the end of the following season and, in true West Ham-style, the club were relegated two years later.

2006/07: A Sicilian nightmare

Alan Pardew’s West Ham side had managed to exceed expectations upon their return to the Premier League, achieving UEFA Cup first-round qualification after their run to the 2006 FA Cup Final to Liverpool, and were drawn with then-Serie A side Palermo.

Anglo-Italian relations did not get off to the most agreeable of starts as several West Ham fans snapped up several ill-advised custom-design T-shirts bearing the slogan “The Hammers vs The Mafia” outside Upton Park before the first leg.

Expectation had been high after the club had only weeks before stunned the football world by announcing the signing of Argentinian internationals Carlos Tevez and Javier Mascherano.

Both players were given their first starts as West Ham lost the first leg to a clinical Andrea Caracciolo penalty-box finish on the stroke of half-time. 

The second leg was simply a disaster of seismic proportions for both team and club.

Before the game, large groups of West Ham fans engaged in running battles with local fans and police, resulting in the city’s Teatro Massimo district resembling a scene from Danny Dyer’s International Football Factories.

The West Ham supporters who had managed to avoid being arrested before the game occupied a large corner of the Stadio Renzo Barbero and, accustomed to their team’s customary cup competition ineptitude, would not have been shocked by the display that unfolded in front of their eyes.

Pardew went for a bold team selection with an attacking trio that included Marlon Harewood, Carlton Cole and Tevez, all of whom spurned chances in a first half dominated by West Ham, the pick of which was an acrobatic overhead kick from Harewood brilliantly saved by the 39-year-old Palermo keeper Alberto Fontana who inexplicably showed the reflexes of a stopper half his age.

Before half-time, West Ham were made to pay for their profligacy when they conceded from a shortly-taken free-kick and their misery was compounded by shipping two second half goals on the counter-attack while chasing the tie.

Their European dream had again been dashed before it had even started and Alan Pardew was sacked ten weeks later.

2015/16: Fair Play “Champions”

By the end of Sam Allardyce’s tenure at the club, West Ham boasted the enviable honour of topping the Fair Play League.

Entering the first qualifying round on July 2, West Ham made it smoothly past Andorran side Lusitanos, despite an early red card for Diafra Sakho.

The second round was less plain sailing for a side transitioning to a change in management style under Slaven Bilic, requiring a penalty shootout to progress past plucky Maltese side Birkirkara FC after again going down to ten men following a James Tomkins dismissal for an innocuous shove to record West Ham’s second red card in as many rounds.

Romanian side Astra Giurgiu, conquerors of Inverness Caledonian Thistle, were their third-round opponents.

They looked in cruise control for the first hour of the game until, almost fatalistically, they self-destructed when James Collins saw red for a second yellow.

West Ham’s “fair play” tag had gone from being an amusing joke to be an entirely farcical notion.

Predictably, they conceded twice in the final twenty minutes – the second a desperate clearance from Angelo Ogbonna that looped over his own goalkeeper – to hand control of the tie back to the Romanians who won the second leg 2-1 over a youthful Hammers side.

2016/17: “Oh not them again?”

A memorable farewell to the Boleyn Stadium had delivered a seventh-place finish, earning a Europa League third round qualifying spot thanks to Man Utd’s FA Cup Final victory, their fans still delirious from the scintillating football played by their Dimitri Payet-inspired team.

Making their debuts at their new London Stadium home, expectation was higher than ever welcoming NK Domžale of Slovenia, who were dispatched with a comfortable 3-0 win, a week after a less-convincing performance in the 2-1 away defeat.  

All eyes were eagerly tuned in to see who would stand between them and the seemingly elusive Europa Group Stages.

Enter a familiar name that still occupied the headspace of many a Hammers fan: Astra Giurgiu, last season’s third-round opponents.

This time Bilic’s men faced the trip to Southern Romania first, and came away with a 1-1 draw in a largely uneventful game.

The return leg was arguably the toughest exit for Hammers fans to stomach; eliminated by a side that had only won one of their five domestic games, despite dominating proceedings from the first minute and missing a hatful of chances.  

They fell behind on the stroke of half-time during a rare opposition counter-attack and despite seventeen unsuccessful attempts on goal – including two unaccountable point-blank stops from the Romanian stopper – they trudged off at full-time, eliminated at the same stage and to the same team, to the full chagrin of the crowd.  

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