The Chilean has won competitions with six clubs in four different countries and is now eyeing more silverware with City.
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Comparing City to Real, Pellegrini said: "It is difficult to compare. Different club, different leagues but it is a very good squad.
"I won several titles in South America but here in Europe it is very difficult to win titles with Villarreal and with Malaga.
"But to be the manager who had the most successful career with these teams is very important for me, the same importance as a title.
"Real Madrid was special, a very good squad but there are a lot of things you must have, not only a good squad, to win."
Pellegrini's men are fourth in the Premier League ahead of Saturday's trip to Fulham.
City's home form, meanwhile, has been exceptional, with a 100 per cent winning record at the Etihad this term producing 35 goals in eight matches.