7 most embarrassing friendly results of all-time – including Dundee 2-0 Man City

Pre-season friendlies, the weird and wonderful of the football calendar: have you ever wanted to see a club side take on a national side? How about West Ham and Manchester City square off in Iceland?

Well, look no further than pre-season. But results don't always go the way that the big teams might hope – and it's led to some embarrassing gaffes.

From Manuel Pellegrini & Co struggling against Dundee to Leeds United losing to a selected side from a war-torn nation, pre-season has it all. And Daily Star Sport is looking at seven of the most embarrassing pre-season results of all time.

Manchester City 0-2 Dundee (2014)

Fresh off the back of their second Premier League triumph, City crossed the border up north to take on Dundee in a routine pre-season contest, or so they thought.

Gary Harkins opened the scoring, before Luka Tankulic, who was on trial on the Scottish side, doubled the tally. City slumped to the embarrassing defeat before a tough campaign.

City had fielded a squad of stars too: Jesus Navas, Stevan Jovetic, and Alvaro Negredo all made appearances.

What is the most embarrassing pre-season result of all time? Let us know in the comments section

Walsall 2-0 Ajax (2018)

"Yes, that really did happen," said the Walsall Twitter account moments after the full-time whistle was blown at Banks's Stadium in 2018.

Erik ten Hag has arrived in the Black Country with his Ajax squad at full strength: Frenkie de Jong, Kasper Dolberg, and Ryan Gravenberch all started. And all were hapless to stop Andy Cook from bagging a brace to lead his side to victory.

To be fair to the Amsterdam-based side, they had already played Wolves earlier that day.

Juventus 1-1 Notts County (2011)

Okay, yes, we're slightly cheating with this one, as it's a mid-season friendly, but it's not every day Notts County hold Juventus to a stalemate.

When Juventus first came into being, the Old Lady adopted Notts County's black and white stripes for themselves. So it was a no-brainer when it came to deciding who to play for the opening of the Allianz Stadium in 2011.

Juve probably didn't think the then League One outfit would hold them to a draw.

Leeds United 1-2 Myanmar All-Stars (2018)

Leeds made some baffling decisions before Marcelo Bielsa rocked up at Elland Road to return the Peacocks to the promised land.

A couple of months before the Argentine arrived Leeds went on a tour of war-torn Myanmar – which at the time the UK government recommended avoiding all travel.

And Paul Heckingbottom's side went on to lose their opening clash to the selected side from the Myanmar National League 2-1, one to forget for Leeds fans.

Tottenham 0-4 Japan (1991)

It was only a matter of time before Tottenham found a spot on this list, a pre-season loss to an unfancied opposition, it's the definition of 'Spursy'.

The 1991 Kirin Cup might be the strangest collection of four sides for a pre-season tournament ever: Japan, Thailand, Vasco da Gama, and Tottenham.

Spurs drew with the Brazilian side, before beating Thailand. But it's the 4-0 slip up to Japan that raises eyebrows.

Nelson 4-2 Real Madrid (1923)

Next summer will mark 100 years since 'little old Nelson' travelled to Spain and conquered the mighty Real Madrid 4-2.

To be fair, Real Madrid were still nine years away from conquering Spain. But in the years since, Real have gone on to conquer Europe, multiple times over, while Nelson have turned into a hangover from the yesteryears of football.

These days, Nelson can be found in the National West Counties Football League, squaring off with sides such as Ilkley Town, Runcorn Town, and Darwen.

Motherwell win the Copa del Rey (1927)

How could we leave this little tale off this list, Motherwell once – unofficially – won the Copa del Rey in pre-season.

The official role of honour has Real Union as the 1927 winners, but they put a special 'commemorative' title on offer, WWE style, in a fatal-four-way between Union, Real Madrid, Swansea, and Motherwell.

Motherwell beat Swansea before brushing off Real Madrid to become the only foreign side to win the Copa del Rey – yes, we're counting it.


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