Andy Roddick, the last American man to win a Grand Slam singles title, accomplished most of his lofty career goals. He reached No. 1 and won the US Open and the Davis Cup. The one goal he just missed out on was winning Wimbledon.

The retired 36-year-old looks back at the 2009 final at the All England Club, where he lost a painfully close match to Roger Federer exactly 10 years ago. Roddick contested the Wimbledon final in 2004 and 2005—losing to Federer both times—but the 5–7, 7–6 (6), 7–6 (5), 3–6, 16–14 loss in '09 was hands down the closest he got to holding the coveted crown.

"It made my life a lot easier when I stopped trying to compare myself to Roger," Roddick said at his induction ceremony to the Hall of Fame in 2017. "It's insane. Certainly no one knows more about what Roger is capable on the court, but me and a couple of others."

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WATCH: Roddick looks
back on 2009
Wimbledon final

WATCH: Roddick looks back on 2009 Wimbledon final