Tipsarevic, ranked ninth, was broken twice in the opening set but bounced back to put away the unseeded Simon in 2 hours, 24 minutes at Ariake Colosseum
No. 4-seeded Juan Monaco of Argentina routed qualifier Grigor Dimitrov of Bulgaria 6-2, 6-1 in another first-round match.
Top seed and defending champion Andy Murray was scheduled to meet Lukas Lacko of Slovakia in a second-round match later Wednesday.
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