It was by the same scoreline that Spurs fell to defeat in Premier League action at the weekend too, going down against relegation battling Wolves and turning in a performance that left stand-in boss Cristian Stellini “angry”.
The return of full-time boss Antonio Conte after a medical absence should buoy Spurs as they seek to overturn a first-leg deficit for the third time in four such instances in European competition.
Conte’s return could perhaps be the best omen of all for Spurs given the Italian boss has won five of his last six managerial home games against Milan in all competitions.
Milan suffered a similarly poor domestic result at the weekend, going down 2-1 against Fiorentina as they lost ground in the race for second in Serie A, with their away form much to blame for their failed title defence this season.
That was a far from ideal warm-up ahead of this trip to North London, with five defeats from their last six two-legged knockout ties against English opposition threatening to wreak havoc to their chances of securing a first UCL quarter-final appearance in 11 years.
Further highlighting why they start this game as outsiders, they’ve also lost by an aggregate 9-1 score on their last three visits to the English capital in European competition.
But if it’s historical omens they’re looking for to inspire them, then 37 wins out of 43 UEFA competition ties in which they won the first leg at home should give Stefano Pioli’s side some belief.
Key battle: Harry Kane, Tottenham’s go-to man on the big occasion, has scored six goals in his last six UCL games at the Tottenham Hotspur Stadium and his last four club goals have been the game’s last.
Aiming to marshall Tottenham’s all-time leading scorer is former Chelsea man Fikayo Tomori, who has been carded in three of his five UCL appearances this term.
Hot stat: Tottenham have conceded the first goal in five of their seven UCL games this season.
