Stefano Pioli is relishing Tuesday's meeting with old foe Antonio Conte as Milan prepare to host Tottenham in their first outing in the Champions League knockout stages since 2014.
Milan finished second to Chelsea in Group E to progress to the last 16 for the first time since the 2013-14 season, when they were hammered 5-1 on aggregate by Atletico Madrid.
Conte's Tottenham stand between Milan and a spot in the last eight, with the former Juventus and Inter boss one of five Italian coaches still present in the competition.
Conte has won eight of his last nine games against Milan (L1) in a run dating back to 2013, and he joins Pioli, Inter's Simone Inzaghi, Napoli's Luciano Spalletti and Real Madrid's Champions League specialist Carlo Ancelotti on an impressive list of Italian bosses to escape the group stage.
Asked who was the strongest of those coaches at Monday's pre-match press conference, Pioli said: "Ancelotti is a symbol but so are Conte and Spalletti.
"There are lots of good coaches, we have a good school and important characteristics.
"Conte is a great coach and one of the few colleagues who called to congratulate me on the Scudetto last season.
"It will be a difficult challenge, inevitably it will be like this for a quarter-final place. A week ago they beat Manchester City. It will be a great game that we will have to play well."
Despite Milan's absence from the latter stages of the competition in recent years, only Real Madrid (14) can better the Rossoneri's tally of seven European Cup/Champions League titles.
Asked whether Milan's illustrious history in the competition could present a psychological barrier for Spurs, Pioli said: "I can't know what our opponents are experiencing, I know what we feel.
"We are highly motivated and it's normal. We only think up to Tottenham. Winning the Champions League is a dream today but it's useless to think about it now."
With Milan 18 points adrift of Serie A leaders Napoli and suffering defeats in the Coppa Italia and Supercoppa Italiana last month, their Champions League tie against Spurs will go a long way to dictating whether their season is deemed a success.
Speaking to Sky Sport ahead of his press conference, Pioli described the tie as the most crucial occasion of his career.
"They will be the two most important matches of my career, having never played in a Champions League round of 16. We have prepared ourselves in the best possible way," he said.
"Our aim is to play with more pace and intensity, you can't ignore that in these competitions. We have prepared ourselves to be up to it."