Denis Shapovalov’s upset win over Rafael Nadal in the third round of the Rogers Cup on Wednesday was not only the biggest win of his career, but one of the biggest upsets in recent tennis history.

For starters, the 18-year-old Canadian became the youngest player to defeat a top two-ranked player in a complete match since Nadal himself did it when he was 17 against Roger Federer in 2004.

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