Tim Henman's Wimbledon preparations were left in tatters on Tuesday after the former British No. 1 slumped to a first round defeat at Queen's at the hands of Croatian teenager Marin Cilic.
Henman was well short of his best as he squandered a lead in the third set before going down to a 7-6, 2-6, 6-4 defeat.
Cilic had never won an ATP Tour match on grass before and the 18-year-old wild card entry, who is ranked 110th in the world, inflicted a chastening defeat on Henman.
Cilic gifted him a break in the fourth game of the first set but the three-time Queen's runner-up quickly found himself 6-5 down.
Henman broke back to reach the tie-break but Cilic earned four set points and a Henman double-fault handed him the set.
Two early breaks in the second set allowed Henman to send the match to a decisive third set and the Briton broke again in the third.
But just as he seemed to have the match under control, Henman suddenly found himself two break points down.
Cilic lofted a return past his opponent that was ruled out, but the Croat challenged, Hawk-Eye showed the ball was clearly in and it was all-square again.
Cilic held serve and Henman found himself serving to stay in the match. A missed volley gave Cilic two match points and he took the second to condemn Henman to his first Queen's first round exit.
Andy Roddick advanced to the third round with a ruthless 6-4, 6-4 win over Radek Stepanek.
Despite a recent slump, Roddick can call on the expert guidance of his coach Jimmy Connors and the former Wimbledon champion would have been proud of the fierce passing shot that broke Stepanek in the seventh game of the first set.
Roddick held on to clinch the set and cracked the Czech in the ninth game of the second before serving out the match.
Mardy Fish, the ninth seed, crashed out in the first round as big-serving Croat Ivo Karlovic ran out a convincing 6-3, 6-4 winner over the American.
Li Na overcame a sluggish start to defeat Yaroslava Shvedova 4-6, 6-2, 6-0 in the second round of the DFS Classic on Tuesday.
Li struggled early against the Russian teenager but she found her stride in the second set, winning 11 of the last 12 games.
Two seeded players lost in first-round play on Tuesday, as No. 11 Olga Poutschkova was lost 6-0, 6-0 to Angelique Kerber of Germany, and No. 10 Severine Bremond was defeated 4-6, 6-3, 6-4 by Alicia Molik.
Molik will play Vania King in the second round, after the American defeated Brenda Schultz-McCarthy 7-6 (7), 7-6 (7).
Taiwan's Chan Yung-jan also made it into the second round by beating Jamea Jackson of the US 6-3, 6-1.
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