Henman headed to the US Open, his final Grand Slam tournament, in poor form, having won only five matches all season.
However, the 32-year-old shrugged off worries about his injured back to produce a vintage performance against big-hitting Dmitry Tursunov, who had won five of their previous six meetings.
He bowed out to Jo-Wilfried Tsonga, a player 10 years his junior, and admitted: "It's a reflection of why I'm retiring. Tsonga is a classic modern player. The way he serves, the way he hits his forehand, his athleticism. It's phenomenal. That's where it's become harder and harder for me to compete."
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