Tottenham and AC Milan are both 5th in the standings in their respective leagues, and I think Tottenham is much better if you look at their last 5 matches.
however the Champions League is a very important competition and even though they are not doing well in their respective leagues there is a possibility in the UCL they will do very well because UCL is a very prestigious competition from other leagues. so of course all players and coaches will try their best to play very well in order to win the match, and it will be a very interesting match.
Tottehham have a good team and they have better form in this season but in Champions League, newbies can feel fearful and lose themselves. Tottenham are not newbies in Champions League but they can not compare with AC Milan about this.
The style of Serie A can control Premier League style very well and AC Milan have a chance to succeed but if someone believe more in recent form, Tottenham would be a winner. AC Milan only can be winner if they make big surprise for Conte and Tottenham.
Yup, I'm not saying AC Milan will easily win this match. Because, so far AC Milan performance is not good. Tottenham will adopt playing fast, same as in the EPL, while AC Milan is playing with more slower. With a different tempo, a different physique, AC Milan will likely prioritize defensive play and counterattack. If they keep up with fast games like EPL teams, it seems Milan is still can't keep up with Tottenham. Milan must be take advantage as a host. If Milan can scored 2 goals and keep cleansheet, maybe Milan have a chance to going to the next round.
The tradition of Italy clubs is playing with slow intensity and prioritizes defense. Premier League and England have a different traditional style, with faster intensity but one point we should know. The coach of Tottenham Hotspurs is Conte who is an Italian coach. Since his coach career debut, he has never prioritized attacking so seriously. With importance of these matches, I think Tottenham will not play too aggressive attacking and we can have very boring matches between Tottenham and AC Milan.