The clock is ticking on Bernard Tomic's French Open preparations after the Australian squandered a strong start to lose in the first round of the Italian Open.
Tomic, who disappointed in Madrid last week after a quarter-final showing on clay in Istanbul, went down to Jan-Lennard Struff of Germany, 6-7 (10-8) 6-1 6-4.
After winning a tight first set and having break opportunities on Struff's serve in the first two games of the second set things began to unravel for the world No.40.
Struff rattled off five straight games to take the set and momentum into the decider.
Things were evenly poised until the ninth game when Struff broke Tomic before serving out the match.
Tomic has typically struggled on clay and at best now can enter a few minor tournaments before the start of the French Open at the end of the month.
Meanwhile compatriot Nick Kyrgios will have to contend with a rough draw in Rome when his campaign gets underway on Tuesday.
Kyrgios will play accomplished clay courter Roberto Bautista Agut in a first round encounter, a win likely to see him up against another Spanish red dirt specialist, Pablo Carreno Busta.
Carreno Busta took out the Estoril Open in Portgual earlier this month.
If successful world No.2 Novak Djokovic looms next for world No.18 Kyrgios.
It was a day of smooth sailing for most of the seeded men with Belgian ninth seed David Goffin through over Brazil's Thomaz Bellucci 6-7 (7-5) 6-3 6-4 and 12th seed Tomas Berdych defeating German Mischa Zverev 7-6 (9-7) 6-4.
Grigor Dimitrov was arguably the most unlucky man at the tournament and was sent packing by an unseeded Juan martin del Potro 3-6 6-2 6-3 while 11th-seeded Frenchman Lucas Pouille also made an early exit, beaten 7-6 (8-6) 7-6 (10-8) by America's Sam Querrey.
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