The match between Milan and Tottenham will be one of the most exciting. Both teams are getting surprising results in their respective leagues. Both of the two matches they will play together may result in surprise results. Since the first match will be in Italy, I think Milan is closer to victory. The second game is in England and anything can happen. I think Milan could be the team that will pass the tour. It's going to be a nice matchup, with two teams of equal strength after all.
From the standings position in their respective leagues, Tottenham & Milan maybe equal from the strength. However, if we look at it from the coach's, Conte seems to be able to understand the character of AC Milan. This is an advantage for Tottenham to be able to beat AC Milan. From AC Milan side, the UCL is an important competition, but a loss to Sassuolo in the domestic league will make Milan players getting bad mentality. Before the game against Tottenham, Milan will meet the two teams that have beaten them, Inter Milan in the Supercoppa and Torino in the Coppa Italia. Obviously, the results of this match will further affect the mentality of AC Milan players. IMO, draw is best results for Milan, and if Milan can win the match, I will be surprise.
Even though Conte knows the characteristics of AC Milan very well, it does not mean that Spurs can easily overthrow Milan. moreover, this match will take place at the San Siro in the first leg at home to Milan. after all, the Spurs also did not show consistent performance in their domestic league. even when in the group D phase, the Spurs had to work hard to get into the last 16.
Meanwhile, Stefano Pioli's squad also did not show good performance, they were defeated by Lazio and Sassuolo in their last two matches. not much the same as Spurs, previously Milan also had to struggle and work hard to qualify while still in the group E phase. I think this battle is a balanced match, both teams do not show strong dominance to win the game later. Both of these teams have the potential to overthrow each other in their respective home matches. however, due to the first leg at home to Milan. I think Milan will take the momentum to win the battle at their own base.