Tottenham boss Antonio Conte has faced Milan 14 times as a coach, winning 10 and losing just once.
The defending Serie A champions have been paired with the North Londoners in the Champions League Round of 16.
Conte has already met the Rossoneri 14 times as a coach and has an almost perfect record.
He’s won 10 meetings against Milan, drawing three and losing once.
His only defeat came in a Milan derby in October 2020 when the Rossoneri won 2-1 thanks to a Zlatan Ibrahimovic brace.
Milan and Tottenham met four times and the Rossoneri were eliminated on both occasions.
The first two meetings were in the UEFA Cup semi-finals when Spurs won 3-2 on aggregate and eventually lifted the trophy in the final against Wolves.
The last two games were in February-Mach 2011. Once again, Tottenham qualified for the following phase – the Champions League quarter-finals, thanks to a 1-0 win on aggregate.