How big-name dropouts fared in the Europa: Man United have been here before...

Louis van Gaal’s lot are the headline act of the last 32 in Europe’s secondary competition, but they’re by no means the first heavyweights to drop into it...

1. Arsenal 1999/2000

Arsenal avoided Europa League ignominy by beating Olympiakos 3-0 last week, just over 15 years since they dropped into the UEFA Cup after losing to Fiorentina in the 1999/00 Champions League.

Arsene Wenger’s charges gave the competition a good go, reaching the final by defeating Nantes and Deportivo 6-3 on aggregate, Werder Bremen 6-2 and Lens 3-1. Galatasaray stood between the Gunners and the trophy; after a goalless 120 minutes, it was the Turkish outfit who held their nerve in the shoot-out, with Davor Suker and Patrick Vieira’s missed penalties proving costly.

2. Barcelona 2000/01

It’s almost impossible to imagine Barcelona competing in the Europa League these days, but in 2000/01 they were unable to advance from a Champions League group ahead of Milan and Leeds United (that’s not a typo, kids) and spent the second half of the campaign playing in the UEFA Cup.

Club Brugge and AEK Athens were brushed aside – a certain Luis Enrique netted four goals over two legs against the latter – before a narrow away goals victory over fellow Spanish side Celta Vigo in the quarter-finals. Liverpool in the last four was a step too far, however: the Reds, who ran out 5-4 winners over Alaves in the final, won a tense tie 1-0 on aggregate, Gary McAllister netting the only goal from the penalty spot in 180 minutes of action.

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3. Liverpool 2002/03

Two wins in six Champions League games against Valencia, Basel and Spartak Moscow meant Liverpool were demoted to the UEFA Cup, where Gerard Houllier’s men made it through to the quarter-finals after beating Vitesse (minus Chelsea loanees) and Auxerre in the two previous rounds.

Celtic were their opponents in the last eight in a highly anticipated ‘Battle of Britain’. Liverpool looked to be in pole position heading into the encounter at Anfield after Emile Heskey’s strike had cancelled out Henrik Larsson’s opener at Parkhead, but Celtic were excellent in the second leg and booked their place in the semi-finals with a 2-0 win on Merseyside thanks to Alan Thompson and John Hartson's cracker with 10 minutes left. How they’d love to even get out of a group these days.

4. Inter 2003/04

Finishing behind Arsenal in the Invincibles season was forgivable, but it was a major surprise when Inter failed to beat Lokomotiv Moscow to second spot in Group B of the Champions League in 2003/04.

The Nerazzurri were welcomed into the UEFA Cup with a ‘glamour’ tie against Sochaux, which was negotiated in rather unconvincing fashion. A 4-3 aggregate triumph over Benfica in the fourth round temporarily quelled the San Siro natives’ unrest, but Inter – clearly not too enthralled by their presence in the tournament – were put out of their misery a few weeks later, a Didier Drogba-inspired Marseille winning both legs against the then-13-time Italian champions. L’OM reached the final, where they lost 2-0 to Valencia.

5. Valencia 2004/05

Valencia may not be considered one of Europe’s elite at present, but they went into the 2004/05 campaign having won La Liga twice in the past three years. That wasn’t enough to get them through a Champions League group featuring Inter, Werder Bremen and Anderlecht, though, and despite being the reigning UEFA Cup champions, they were unable to beat Steaua Bucharest in the last 32 despite winning the first leg 2-0. A disappointing season was rounded off with a seventh-place finish in La Liga, their worst since 1998.

6. Juventus 2009/10

No Fulham fan will ever forget their side’s sensational comeback against Juventus in the last 16 of the Europa League in 2009/10. Trailing 3-1 from the first leg, Roy Hodgson’s men fell behind after two minutes at Craven Cottage, before remarkably netting four times to knock the Old Lady out in dramatic fashion.

Yet to fully recover from the Calciopoli scandal that culminated in relegation to Serie B in 2006, Juve were taking the competition seriously as they searched for their first major (unrevoked) trophy in seven years. Gianluigi Buffon, Fabio Cannavaro, David Trezeguet & Co. were left stunned by plucky old Fulham, though, with the Cottagers making it all the way to the final (more on that next).

7. Atletico Madrid 2009/10

Like Juventus, Atletico Madrid were also relegated to the Europa League in 2009/10 after finishing third in a Champions League battle with Chelsea, Porto and APOEL. Unlike Juventus, their participation in the continent’s junior club competition was highly successful.

After defeating Galatasaray 3-2 on aggregate in the first knockout round, Quique Sanchez Flores’s Atleti overcame Sporting Lisbon, Valencia and Liverpool on away goals to set up a final with Fulham. There, a brace from Diego Forlan – supported up front by Sergio Aguero – gave Atletico their first continental prize since the European Cup Winners’ Cup of 1962.

8. Manchester United, 2011/12

This isn’t the first time United have been in this situation: four years ago, the Red Devils were dumped out of the Champions League following a final-game defeat to Basel.

After edging out Ajax in the last 32, United fell victim to Marcelo Bielsa’s wonderful Athletic Bilbao team, who played some truly dazzling football as they won at both Old Trafford and San Mames (the clash at the latter featured one of the greatest ‘nearly goals’ of all-time, below) with future United man Ander Herrera in midfield. Midtjylland are unlikely to pose quite as many problems this season, but then Louis van Gaal’s United have proved quite capable of making plenty of their own in recent times.

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9. Chelsea 2012/13

Chelsea’s extraordinary decline means that a Europa League place is probably the most Jose Mourinho can hope to achieve this term. Qualification for next year’s edition could potentially put the Portuguese in a rather difficult position, however; when one of his many arch enemies Rafael Benitez led the Blues to the trophy as interim manager in 2013, Mourinho wasn’t exactly forthcoming with praise, insisting that winning the competition “would be a big disappointment for me”.

Chelsea dropped into the tournament three seasons ago after finishing third in a Champions League group containing Juventus, Shakhtar Donetsk and Nordsjaelland. Benitez promptly replaced Roberto Di Matteo in the dugout – much to the dismay of most fans – and oversaw victories over Sparta Prague, Steaua Bucharest, Rubin Kazan, Basel and Benfica to ensure Chelsea supporters could continue with the “champions of Europe, we know what we are” chant that was first sung after the previous year’s unlikely European Cup final triumph over Bayern Munich.

10. Juventus 2013/14

The major criticism of Antonio Conte at Juventus was his team’s inability to translate their domestic dominance into European progress. While their progression into the quarter-finals of the Champions League in 2012/13 was a good achievement, the Bianconeri’s failure to advance ahead of Galatasaray in Group D the following year was a clear setback.

The fact that the 2014 Europa League Final was due to be held at Juventus Stadium was seen as perfect motivation for the Serie A giants, but a loss to Benfica in the final four meant Juve were unable to participate in the Turin party on 14 May.

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