Pep Guardiola had the chance to undo the hoodoo at Spurs’ new stadium on Tuesday night.
And he blew it.
Son Heung-min’s winner ensured Man City’s decorated gaffer endured another dose of Champions League quarter-final frustration away from home.
Guardiola has won just one away Champions League quarter-final in his managerial career — a 1-0 win away to Shakhtar Donetsk with Barcelona in 2011.
Let’s run through his eight victory-less instances…
2009 Bayern Munich 1 Barcelona 1
In fairness to Pep, we must recognise that the early days of the hoodoo were not considered troubling in the slightest.
His Barca side demolished Bayern 4-0 at the Nou Camp in the first leg with Thierry Henry, Samuel Eto’o and Lionel Messi (x2) all cashing in.
With the job already done, the 90 minutes in Bavaria were a formality — no criticism for not getting the win here.
2010 Arsenal 2 Barcelona 2
A Zlatan Ibrahimovic brace put the visitors 2-0 up as Henry soaked up applause on his return to North London.
But a late comeback propelled the hosts away from defeat — Cesc Fabregas converting a 85th minute penalty after Theo (three-o) Walcott had got one back.
Arsenal fans were optimistic of a result in the reverse fixture as both Carles Puyol and Gerard Pique were suspended.
Unfortunately for them, Messi happened.
The Argentine No10 scored four goals in a memorable performance to dispatch the Gunners — you remember.
2012 Milan 0 Barcelona 0
Some genuine frustration here.
Barcelona hadn’t been denied a goal in a Champions League fixture for two and a half years until Milan coupled last-ditch defending with some good fortune.
This was the first instance Guardiola was accused of failing to react to the match dynamic in an away quarter-final.
Though in truth, it took some special blocks from Alessandro Nesta and Massimo Ambrosini to deny Messi and co.
2014 Man United 1 Bayern Munich 1
A classic Champions League match-up, but it’s worth noting the two teams’ respective status at the time.
United were labouring under David Moyes and had suffered comprehensive home defeats to rivals Liverpool and Man City in the build-up to the European showdown.
While Bayern had installed Guardiola after winning the treble the season previous.
Many United fans feared a thrashing but Nemanja Vidic gave the hosts the lead with a towering header as part of a spirited performance.
You may remember Danny Welbeck was one-on-one with Manuel Neuer and tamely chipped his finish into the German’s hands…
Bastian Schweinsteiger’s equaliser ensured the tie was in Pep’s hands but by this stage he was probably mildly concerned about his record away from home in the knockout latter stages.
2015 Porto 3 Bayern Munich 1
This was a big one.
Ricardo Quaresma bagged twice in the first ten minutes as Bayern’s defence exhibited the kind of nervousness that would later inflict Guardiola’s City side at the same stage.
Neuer could have seen red early on while Dante and Jerome Boateng gave Porto reasons to be optimistic at every turn.
However, Bayern rallied to win the second leg 6-1 — they were even 5-0 up at half time.
2016 Benfica 2 Bayern Munich 2
Problems in Portugal again.
Raul Jimenez, now of premature mask fame, put Benfica ahead to cancel out Bayern’s slender 1-0 lead from the first leg in Munich.
Arturo Vidal and Thomas Muller put the visitors in control but it required a distinctly un-Guardiola performance to prevail.
Javi Martinez should have been sent off for a professional foul and while the tie was never really in doubt, the game certainly could have gone the hosts’ way with a slither more luck.
Talisca’s free-kick levelled to continue Guardiola’s winless streak away from home in Champions League quarters.
2018 Liverpool 3 Man City 0
At the time of this fixture, City were closing in on a record-breaking Premier League season with unprecedented swagger.
But everyone suspected Liverpool were the Kryptonite to English football’s Superman.
Overwhelmed by the occasion (facilitated by a hostile welcome from the Anfield faithful) City crumbled to Jurgen Klopp’s heavy metal football, conceding three goals in 19 breathless first-half minutes.
Unlike previous quarter-finals, Guardiola was unable to make up the difference at home.
2019 Spurs 1 Man City 0
Sergio Aguero’s missed penalty, Son’s goal… you don’t need reminding of this one, it happened this week.
Not for the first time, people have questioned whether Guardiola overthought his tactics and team selection at this stage of the tournament.
Fabian Delph, Riyad Mahrez… a distinct shortage of Leroy Sane and Kevin De Bruyne.
Could it be that his decision-making in such games is now affected by history?
Despite just one away win in nine, Guardiola has been successful in all but one of his Champions League quarter-finals as a manager — an undeniably impressive feat.
Spurs only have last year’s Liverpool side to take for inspiration ahead of the second leg at the Etihad on Wednesday.
Regardless of the outcome in Manchester, we await Guardiola’s Champions League away quarter-final next season with baited breath…