Spaniards David Ferrer and Juan Carlos Ferrero also suffered first round shocks at the Valencia Open on Tuesday.
Holders Croatia had to be content with a win and a loss from the opening day's two singles rubbers in the Davis Cup.
In women's action, comeback queen and former world number one Martina Hingis beat Austria's Sybille Bammer at the Pacific Life Open.
Andre Agassi slumped to a 7-5, 7-5 defeat against Bjorn Phau at the Dubai Open
The world number one was pushed by the Russian but survived to book his place in the last four of the Australian Open against German Nicolas Kiefer.
Roger Federer produced an imperious display to dismiss unseeded German Florian Mayer 6-1, 6-4, 6-0 in the second round
Russia's Nikolay Davydenko earned the semi-final berth by beating Gaston Gaudio 6-3, 6-4.
Andre Agassi was swept aside 6-4, 6-2 by Russian Nikolay Davydenko at the Masters Cup
The Argentine ace would have made sure of a berth in the year-end Masters Cup in Shanghai had he not lost to Czech Tomas Berdych.
The unseeded Thai will face Italian David Sanguinetti, who upset number 31 Carlos Moya, in the second round at the US Open.
The top seed beat Mariano Puerta in 72 minutes to set up a semi-final with France's Paul-Henri Mathieu in the Montreal Masters.
Philipp Kohlschreiber upset world No 4 Nikolay Davydenko to put Germany level after Igor Andreev trounced Germany's No 1 Tommy Haas in the opening rubber.
The Spaniard beat Tomas Zib 6-2, 6-1 to register his 32nd successive win on clay.
Russian Nikolay Davydenko saw off Tommy Haas in the U.S. Open quarter-finals for the second successive year, beating the German 6-3 6-3 6-4 on Wednesday to reach the last four without dropping a set.
The world number one battled back from a break down in the final set to fend off the Aussie and reach the final of the Cincinnati Masters.
The top seeds eaily beat the Russian pair of Denis Golovanov and Andrei Olhovskiy in a quarter-final match at the Moscow ATP event.
The Second seed Andy Roddick went through after Russian Nikolay Davydenko retired in the third set of their match because of breathing problems.
A subdued Tim Henman was overpowered by Russia's Nikolay Davydenko 6-4, 6-2, 6-2 in the third round.
The World number one won his 20th consecutive match on Friday as he breezed past Russian Nikolay Davydenko 6-3, 6-4.
Roger Federer cruised into the semi-finals of the Qatar Open with a 6-1, 6-2 demolition Feliciano Lopez.
Germany's Tommy Haas beat third seed Nikolay Davydenko 6-3, 2-6, 1-6, 6-1, 7-5 to enter the semi-final.
The Argentine No 1 overpowered Russia's Marat Safin in the second singles after Nikolay Davydenko beat Juan Ignacio Chela.
The win gave the Russian his third title of the year.
Sweden's Jonas Bjorkman defeated the world number one 6-3, 6-4 in just over an hour at the Qatar Open.
A round-up of Day 4 at the second Grand Slam of the year.
The tenth seed was beaten by Slovenia's Tina Pisnik in the second round at the French Open.
Ivan Ljubicic salvaged the opening day of Croatia's Davis Cup semi-final against Russia, winning a pulsating five-set duel with Mikhail Youzhny to level the tie 1-1.
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