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Tennis fans will tell you that the Stefanos Tsitsipas experience is not for the faint of heart.
Sometimes, the impeccably styled Greek player appears unbeatable, but too frequently, he seems to lose his focus. Formerly ranked third worldwide, Tsitsipas has dropped to the 30th spot and hasn’t strung together three consecutive wins since March when he claimed a title in Dubai, followed by two wins in Indian Wells.
At the time of that streak, Tsitsipas was ranked No. 8 and looked like he was on the cusp of a resurgent season.
Instead, the 26-year-old won nine of his next 17 matches and is now in danger of losing his seeded status for the US Open.
ATP Toronto: Stefanos Tsitsipas vs. Christopher O’Connell
Tsitsipas’ off-court dramatics always follow him around, and things are quite noisy right now.
Adding to the turbulence, Tsitsipas’ high-profile relationship with WTA star Paula Badosa has ended, and he parted ways with his coach, Goran Ivanisevic, just before the North American hard court season began.
This change might be what Tsitsipas needs to finish the year on a high, but it’s concerning because there always seems to be a disruption within his team.

Tsitsipas remains one of the most talented players on the ATP Tour and can play an opponent like Christopher O’Connell off the court, but at the same time the Aussie is the exact type of foe that can be a thorn in the side of a hot-headed favorite.
O’Connell won’t cede an inch, knowing he just needs to hang around in the match as long as possible in order to give Tsitsipas the runway to unravel.
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O’Connell had a very disappointing campaign on the grass, but he’s never seemed comfortable on the surface and should be buoyant after a dominant win over Chun Hsin Tseng in Round 1 in Canada.
Tsitsipas could make quick work of O’Connell, but it’s more likely that this match has plenty of twists and turns.
The Play: Over 23.5 Games (bet365)
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Michael Leboff is a long-suffering Islanders fan, but a long-profiting sports bettor with 10 years of experience in the gambling industry. He loves using game theory to help punters win bracket pools, find long shots, and learn how to beat the market in mainstream and niche sports.