Photo via si.com
Result: Defeated Mark Philippoussis
A young Roger Federer announced himself to the world by claiming his first major title at the All England Club in 2003. At the time, his style hadn't quite caught up to his success. Rocking a ponytail, a headband, and a plain, slightly oversized white and gray shirt to match his white and gray shoes, Federer looked very much like a 21-year-old on the big stage for the first time.
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