A strong favorite in any tournament she competes in, Williams was unable to summon her championship grit as she fell to the 13th seeded Greek on a rain-delayed Tuesday night. Sakkari was able to pull off the upset, defeating the two-time Cincinnati champion 5-7 7-6(5) 6-1 after two hours and 16 minutes.

Williams raced to a 3-1 lead after an early break but was unable to serve out the first set at 5-4. Sakkari's comeback was halted when she served to take the set to a tiebreak, as Williams strong play saw her clinch the first set.

The second set saw Sakkari break Williams's opening service game and obtain a 3-1 lead of her own. However, the 23-time Grand Slam champion fought back and reeled off four consecutive games to serve for the match. Although she was two points away from victory, Williams was unable to serve out the match and was broken by a revitalized Sakkari. A tiebreak ensued that saw Williams fail to capitalize on a 4-1 lead, as her Greek opponent rallied to level the match.

The final set saw Williams exhibit frustration as she was broken in her first service game. The American also seemed to struggle physically, perhaps still feeling the effect from her battle with Rus in the previous round. Nonetheless, Sakkari dominated the final set to lead 5-0, as Williams continued to commit several of her 58 unforced errors. The American salvaged a game as she served to stay in the match, saving seven match points. However, Sakkari finally crossed the finish line as she converted her eight match point with a backhand winner.

The 13th seed next faces Great Britain's Johanna Konta, who defeated former World No.2 Vera Zvonareva 6-4 6-2 earlier in the day.

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