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What's the worst European defeat for any English club?

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It was a setback in the second game of a rookie’s managerial career. Halmstad got a 2-2 draw at the Estadio da Luz, ensuring their first-leg lead was decisive. Benfica were out of the 2000/01 Uefa Cup. It remained the only time Jose Mourinho was knocked out of the competition in its various incarnations until last month. Until Dinamo Zagreb 3 Tottenham 0. Until the team whose manager was in prison beat the side whose manager should… well, insert your own gag here.

It was a spectacularly bad result. Quite how bad, however, may not have been acknowledged. The worst of Mourinho’s two decades in continental competitions? Definitely. But, arguably, it is the worst by any English club in Europe since 2005.

Consider the evidence. Dinamo will face Villarreal this week in their first European quarter-final since 1970. Regular group-stage participants, either in the Champions or Europa Leagues, have precious little pedigree in the knockout stages. They had not won a two-legged tie against a club from one of the major western European leagues for half a century.

So, while Leicester went out to Slavia Prague, another eastern European side, in the previous round, there are distinct differences. Slavia eliminated the serial Europa League winners Sevilla two years ago. Leicester did not have a first-half lead. The Foxes may be disrupting the Premier League’s big six but they have neither the budget nor the European experience of the regular suspects. Arsenal’s exit to Olympiakos last season felt underachievement but the Greek club are a familiar sight in the last 16 of continental competitions; they often record a group-stage win or two over elite opponents.

And, in the search for a worse result than Tottenham’s capitulation in Croatia, group games should be discounted. Manchester United’s autumn loss to Istanbul Basaksehir was embarrassing but in itself it did not knock them out of the Champions League. The 2011/12 inability to qualify from a group including Benfica, Basel and Otelul Galati was worse in some respects, but attributable to four games against the Swiss and Portuguese clubs.

Examine the Premier League’s representatives’ record in the most prestigious European competition and it reflects the superiority of the top five domestic leagues. Since 2007, every aggregate defeat has come to Spanish, Italian, German, French or other English opposition; even 14 years ago, Arsenal’s loss was to a PSV Eindhoven side who were semi-finalists two years earlier.

In the Champions League, Newcastle lost a play-off to Partizan Belgrade in 2003 and Blackburn endured an ignominious group stage in 1995 but, arguably, no English club has suffered as bad a defeat in a knockout tie as Spurs’ Europa League loss to Dinamo.

There are contenders in the UEFA Cup. Yet the fact that Tottenham were Champions League finalists two years ago and have a squad that includes a World Cup-winning captain, a World Cup Golden Boot winner and a serial Champions League winner should confer an extra level of expectation.


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So, wretched as West Ham’s 2015 exit to Astra Giurgiu, Southampton’s elimination by Midtjylland the same year, Hull’s 2014 play-off defeat to Lokeren and Blackburn’s 2008 first-round loss to Larissa were, none exactly appeared potential winners of the competition. Nor did the pre-Sheikh Mansour Manchester City, who went out to Dyskobolia Grodzisk Wielkopolski in 2003.

Perhaps Everton were not in 2005, either, despite finishing fourth in the Premier League, but a 5-1 thrashing by Dinamo Bucharest means it might qualify as a worse result than Spurs’ 3-0 loss in Zagreb. If not, maybe Chelsea’s 2001 and 2002 first-round exits to St Gallen and Viking Stavanger might trump Mourinho’s troubles in Zagreb. 

The 1995 double bill of United going out to Rotor Volgograd and Liverpool to Brondby stands out for the wrong reasons, along with Blackburn’s loss to Trelleborgs in the same season they won the Premier League. Yet the gulf between the richest and the rest has widened since then. Mourinho, often in charge of one of the wealthiest clubs, has been a beneficiary of that trend.

It should provide a kind of immunity against the sort of upset seen in Croatia. Instead, Mourinho, the manager who long specialised in making history, achieved it in unwanted fashion. Dinamo Zagreb 3 Tottenham 0 was a historic low; not merely for Spurs or for him, but for English clubs in Europe.

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