When Novak Djokovic and Marin Cilic took the court in the second round of the Shanghai Rolex Masters Friday, they collectively entered the history books. The matchup officially became the oldest Masters 1000 match ever played, with a combined age of 75 years and 139 days.

Playing their 22nd match against each other, both men, long past their peak and edging closer to retirement, still managed to produce a contest with more fireworks than many had expected.

How the Match Unfolded

Both players started strong on serve, holding comfortably and offering few chances to break. To the surprise of many, Cilic hung in impressively and was actually the first, and only, player in the opening set to generate break points, doing so in the 11th game.

Using his slice backhand and powerful forehand bri

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