Great Britain's Cameron Norrie and Jack Draper both fell at the first hurdle in the Japan Open on Tuesday.
Norrie faced a baptism of fire against defending champion and top seed Taylor Fritz, who strolled to a 6-4 6-3 win, while Draper was left to rue what could have been in a 6-4 6-7[4] 6-7[1] beating by Alex de Minaur.
Heading into the ATP 500 event in Tokyo, British number one Norrie had endured a dampening three-game losing streak at the top level, losing his opening matches in Beijing and Shanghai over the past few weeks.
Nothing could split Norrie and Fritz in the head-to-head column, as both men boasted six wins apiece from their previous 12 contests, although the former had prevailed in their most recent clash at this year's United Cup.
After missing four break points early doors, Fritz's wasted opportunities almost cost him as Norrie broke in the fifth game and backed it up with a hold to 30, but the defending champion demonstrated his credentials by winning four games on the bounce to steal the opener.
Seven aces and a first-serve win rate of 86% helped Fritz spark a brilliant first-set fightback, and the American dropped just one point in the opening three games of the second set, breaking Norrie to love in game two.
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Despite landing more first serves, Norrie could not make any inroads on the Fritz serve and did not fashion a single opportunity to break back against the top seed, who finished the contest in style with back-to-back aces.
Norrie and Fritz were only on the court for 80 minutes before the latter advanced to round two, but Draper and Australian fourth seed De Minaur engaged in a gruelling three-hour slog in what was the 21-year-old's first ATP Tour match since the US Open.
Draper had taken part in a couple of Challenger events in France to prepare for the Japan Open, where he did not drop a set in two qualifying victories, and the world number 88 was out for revenge against De Minaur following his Wimbledon second-round exit to the Australian in 2022.
Draper was on the path to redemption against the 24-year-old, who conceded two set points with a double fault in the 10th game - which Draper capitalised on - and De Minaur would immediately lose serve in the second set too.
However, the fourth seed found a sixth gear to win four games on the spin, and while Draper got the contest back on serve at 4-4, he could not recover from a poor start to the tie-breaker.
Neither player gave too much away in the decider, but a break for Draper in the ninth game would ostensibly set the Briton on the road to round two, only for De Minaur to immediately break back while the 21-year-old was serving for the match.
As was the case in the second set, a deflated Draper was outgunned in the winner-takes-all tie-breaker, and De Minaur's ninth ace of the afternoon propelled the world number 13 into the last 16.
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