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Reilly Opelka defeats John Isner in four sets at the Australian Open on Monday.

Opelka Shocks Isner To Claim First Grand Slam Victory

Dimitrov through in four sets

In a meeting between two of the tallest players in the Australian Open draw, 6'11" Reilly Opelka caused the biggest upset of the day to beat 6'10" John Isner 7-6(4), 7-6(6), 6-7(4), 7-6(5) on Monday.

The 21-year-old ended Isner's nine-match unbeaten Grand Slam record against American opposition after two hours and 58 minutes, firing 40 aces to record his first Grand Slam victory. Isner also landed 47 aces in a match which featured a combined 143 winners.

Opelka's only previous Grand Slam appearance came as a qualifier in Melbourne, falling in five sets to David Goffin in 2017. The World No. 102 improves to 2-1 against Top 10 players, having also beat then-No. 8 Jack Sock at 2018 Delray Beach.

Opelka will meet Thomas Fabbiano for a place in the third round. The Italian beat Australian wild card Jason Kubler 6-4, 7-6(1), 2-6, 6-3 in three hours and four minutes.

Grigor Dimitrov recovered from a set down to beat Janko Tipsarevic 4-6, 6-3, 6-1, 6-4. The 2017 semi-finalist (l. to Nadal), making his ninth straight appearance at Melbourne Park, fired 42 winners, including 18 aces, to advance after two hours and 33 minutes.

During the off-season, Dimitrov has continued to work with former World No. 1 Andre Agassi in Las Vegas. Agassi began work with the 2017 Nitto ATP Finals champion at the Rolex Paris Masters last November, as Dimitrov looks to make a return to the Top 10 in the ATP Rankings.

"[Andre has] done so much outside of the court," said Dimitrov. "I'm just a better person, period. On a daily basis, I have learned something new from him."

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The 20th seed, who entered the match with a 1-4 FedEx ATP Head2Head record against Tipsarevic, improves to 3-1 this season after a run to the Brisbane International quarter-finals (l. to Nishikori). Former No. 8 Tipsarevic was making his first appearance at any level since the 2017 US Open, following surgery on both hamstring tendons.

Dimitrov will meet Pablo Cuevas in the second round. The 33-year-old Uruguayan needed just over two hours to beat Dusan Lajovic 6-4, 7-6, 6-1.

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