Having won the Italian Cup four times as a player and once as a coach, as well as the European Cup twice as a player and twice more as coach, it was understandable when he titled the book Preferisco la Coppa - I Prefer the Cup.
On Saturday he can write another chapter by winning the oldest cup competition in the world against unfancied Portsmouth at Wembley Stadium to complete the double in a memorable first year in English soccer.
"I did not know before this season how important the FA Cup was for every club," Ancelotti told reporters at Chelsea's Surrey training base on Thursday.
"I know there have been a lot of surprises in this competition - Leeds beat Manchester United and Reading beat Liverpool - so we need to pay attention. On paper we have more quality and possibility to win but we have to play well to win.
GREAT OPPORTUNITY
"My players know very well how they have to prepare and play.
"It's a great opportunity to win the double for the first time with this club but if Portsmouth play better they could win."
Chelsea have won 13 and drawn one of their 14 Premier League meetings with the south-coast club who finished bottom this season, including a 5-0 thrashing at Fratton Park in March, but Ancelotti said Saturday will be altogether different.
"We won and played well but at that time they didn't have a lot of motivation but they will on Saturday and it will be a different game," he said.
"We have to have respect for Portsmouth. They were relegated but they deserve to play in this final after beating Tottenham in the semis. We have to fight against them to win this game.
"It is an opportunity for them to save the season. We have to play against players with strong motivation."
Ancelotti confirmed captain John Terry would be fit to start after his foot injury turned out to be minor but he does have a concern over right back Branislav Ivanovic.
He has a knee injury and if the big Serbian interntional does not recover Paulo Ferreira will start in his place.
‘After Manchester City’s recent form, maybe they’re the underdogs against Manchester United!’ Former Red Devils defender on this weekend’s derby
‘Arteta, Alonso, Emery, me… none of us were physical players – we needed the understanding of the game. That probably helped us move into management’: Premier League boss reveals reasons for natural career progression
