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It wasn’t a banner season for Andy Roddick. He suffered injuries, he lost earlier than usual at majors, his ranking slipped out of the Top 10, and he surrendered his top spot on the U.S. tennis totem pole to his old buddy Mardy Fish.

Still, there was at least one moment to savor. In February, Roddick hit what he called “the best shot ever in my life, considering the circumstance.” It was hard to argue with that—except, maybe, the “circumstance” part. Roddick hasn’t hit many better shots anywhere, anytime than he did to beat Milos Raonic in the Memphis final.

The match between these two bomb throwers had been as close as humanly possible—Roddick won the first set in a tiebreaker, 9-7; Raonic won the second in a tiebreaker, 13-11. Now Roddick, who had been sick that week, was trying to stave off what seemed destined to be a third breaker. At 6-5, 30-40 on Raonic’s serve, Roddick scrambled to his right for a sharply angled volley and dove. As he hit the ground, he poked a forehand up the line for a winner. It was a better result than he’d expected. “He had a great volley there,” Roddick said. “I don’t really remember much else besides the fact that I went for the ball, I hit it, I didn’t really think much of it. Then I heard people cheering. I was like, ‘No, there’s no way that went in.’ I guess it did.”

Roddick had thrown caution to the wind to get this final point. So much so that the baseball cap that he has kept firmly in place in recent years was allowed to fly off. Perhaps apropos of his star-crossed season, the big story the next day wasn’t just his brilliant shot, it was what—or, in this case, wasn’t—underneath that baseball cap. See above.

—Steve Tignor

Look for more Aces & Faults pieces throughout December on TENNIS.com. Here's what we've written about so far.