During Manchester United's title triumph over Chelsea back in 2007, there were more than a few unfavourable remarks and reviews made by the "Special One" about his Portuguese compatriot.Some of the more standout opinions Chelsea's Mourinho had about his then rival club's star player included "immature", "disrespectful" and "ill-educated".
But football can be a funny old game and both men now find themselves having to work together for a common goal - bringing the La Liga title back to Real Madrid.
In their brief time working together so far, they have certainly made an impression this season.
Overcoming a slow start, Ronaldo has fired Real to the top of the La Liga standings with an incredible 10 goals in his last four league games. After only a short time together, Mourinho is already considered as good as United manager Sir Alex Ferguson in Ronaldo's eyes.
"Mourinho is a good coach with a very clear philosophy. Now you can say, already, he is the father of Real Madrid," Ronaldo was quoted in the Daily Mirror as saying.
"He and Sir Alex are so very different but at the same time very similar.
"They share the experience, the winning spirit of victory. Of course, one of them is much older and they have lived through two very different stories.
"But I loved the time I spent working with Sir Alex and have great memories. We built a friendship and now I feel the same feeling with Mourinho. For me they are the two best coaches in the world.
"This year you can see that several things have changed: discipline, aggressiveness, style of play and the willingness to work hard and together towards the same goal. This season is very different from the past. Madrid this year is not last year. We are totally different. "
Mourinho, Ronaldo and the rest of the star studded Madrid team play at the San Siro on Wednesday night where they will put their perfect Champions League Group G record on the line against AC Milan.
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