Though I am quite certain that this is not the extent of his collection, here is a short video interview of Roger Federer discussing three of his Rolex watches — a Day-Date, a 1981 (Federer’s birth year) vintage Rolex Daytona in stainless steel (do I see some a bit of trop dial?), and a Datejust with fluted bezel.  Roger notes that many of his watches are engraved to mark special occasions (such as wins of majors).  Interestingly, he also mentions that he sometimes practices while wearing the Day-Date.  The interview is conducted by Vijay Amritraj, who along with his brothers Anand and Ashok were among the first Indians to play in top-flight international tour tennis.

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Roger Federer’s Rolex Watch Collection (Video)