Briton Dan Evans was beaten in straight sets by Taiwanese Jimmy Wang in the final qualifying round of the Sony Open in Florida, USA.
Wang defeated the British number two 6-4 6-2 to take his place in the main draw of the Miami tournament.
Evans, 23, failed to get half of his first serves in and struggled with his returns against an opponent ranked 145 in the world.
World number six Andy Murray has been given a bye into the second round.
Other big names in the ATP-1000 tournament include Spain's Rafael Nadal, Serb Novak Djokovic, Australian Open champion Stanislas Wawrinka and his Swiss compatriot Roger Federer.
Evans, ranked 127 in the world, beat top-100 player Tim Smyczek 6-4 6-2 in the first qualifying round and reached his maiden ATP Tour semi-final in Zagreb, Croatia last month.
A place inside the world's top 100 would guarantee Evans automatic entry to the main draw of all Grand Slams.
Apart from Murray, the last British player to approach the top 100 was Alex Bogdanovic, who climbed to 108 in 2008.