Day 3 of the Australian Open had a little bit of everything: big upsets, five-set thrillers, nail-biting tiebreaks, huge American wins and battles that stretched past the four-hour mark—and that was just Tommy Paul.

 

Paul (pictured above) logged the biggest win of his career, defeating No. 18 seed and 2017 Australian Open semifinalist Grigor Dimitrov, 6-4, 7-6, 3-6, 6-7, 7-6, to progress to the third round of a major for the first time.

 

Coming into the tournament, Paul had never been past the first round of a Slam in three previous attempts, losing in the first round of the US Open in 2015 and 2017 and in his first match at the 2019 French Open.

 

Paul fell in the second round of qualifying in each of the past two years in Melbourne but is quickly showing he is ready for playing big matches on big stages.

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Of course, Paul hasn’t always been playing primetime matches. After failing to make the main draw in New York in September, Paul continued grinding at tennis’ lower levels. He played Challenger-level events in New Haven, Conn., Cary, N.C., Tiburon, Calif., and Knoxville, Tenn.

 

While considerably lower on the totem pole than the first Grand Slam of the season, Paul played well, winning titles in Tiburon and New Haven, reaching the semifinals in Knoxville and the quarterfinals in Cary. That set him in good stead for a trip Down Under, and he continued his late-fall form with a run to the semis in the Australian Open tune-up event in Adelaide, where he beat three Top-60 players in succession en route to the final four.

 

Fast forward to Wednesday, and the experience and self-belief that Paul has worked so hard to achieve came to fruition.

 

He took the opening set behind a lone break at 4-4, and he won five of the final six points of the second-set tiebreak to put himself on the brink of a major upset. 

 

Dimitrov rallied back in sets three and four to force a decider, but he failed to serve out the match at 5-4 after breaking the American in consecutive games. In the 10-point tiebreak, the pair split the first six points before Paul reeled off the final seven to earn a memorable victory.

 

The win over Dimitrov guarantees that the 21-year-old New Jersey native will take home at least $123,000, with the chance for an even bigger payday when he meets Marton Fucsovics of Hungary in Round 3.

 

Ranked No. 67, Fucsovics has also been playing impressive tennis this week at Melbourne Park, taking out 13th seed Denis Shapovalov of Canada in his opening match and defeating rising teen Jannik Sinner of Italy in straight sets in Round 2.  The winner will advanced to play either No. 3 seed Roger Federer or hometown favorite John Millman in Round 4.

 

Paul was one of nine U.S. players to win singles matches Wednesday, as eight Americans punched their tickets to the Round of 32.

 

Top-ranked American woman Serena Williams needed just 78 minutes to see off Tamara Zidansek of Slovenia, 6-2, 6-3. The 23-time women’s singles champion will play Qiang Wang of China in Round 3, with the possibility of meeting good friend Caroline Wozniacki in the fourth round in what could be the final match of Wozniacki’s career.

 

The Dane announced before the tournament that this will be the last event she plays. And while Serena is chasing down Margaret Court's all-time Grand Slam women's singles mark of 24, she will likely also be feeling strong emotions should the two play in Round 4. 

 

In other women's matches on Day 3, Coco Gauff rallied from a set down to beat Sorana Cirstea of Romania, 4-6, 6-3, 7-5, inside Melbourne Arena to set up a mouth-watering US Open rematch against reigning Aussie Open champion Naomi Osaka.

 

No. 10 seed Madison Keys beat Arantxa Rus of the Netherlands, 7-6, 6-2, and No. 14 seed Sofia Kenin defeated compatriot Ann Li, 6-1, 6-3. Keys will meet No. 22 seed Maria Sakkari of Greece in the third round Friday, while Kenin will meet Shuai Zhang of China for the chance to battle either Gauff or Osaka.

 

No. 18 seed Alison Riske needed a tick more than an hour to beat Lin Zhu of China, 6-3, 6-1, and she will now meet Germany’s Julia Goerges in Round 3 after Goerges rallied to beat 13th seed Petra Martic on Wednesday.

 

Wrapping up the first-round matches that were rescheduled because of Monday’s heavy rain, Taylor Townsend beat fellow American Jessica Pegula, 6-4, 7-6.

 

On the men’s side, Tennys Sandgren defeated eighth-seeded Italian Matteo Berrettini, 7-6, 6-4, 4-6, 2-6, 7-5, and Sam Querrey topped Ricardas Berankis of Lithuania, 7-6, 4-6, 6-4, 6-4. The two Americans will now meet for a spot in the final 16 against either No. 12 seed Fabio Fognini or No. 22 seed Guido Pella.

 

Elsewhere on Day 3, wild card Michael Mmoh gave No. 9 seed Roberto Bautista Agut an early scare before falling, 5-7, 6-2, 6-4, 6-1, and qualifier Caty McNally lost to Zhang, 6-2, 6-4.

 

Doubles play also began Wednesday, with Mike and Bob Bryan, playing in their 21st and final Australian Open, advancing to the second round with a 6-1, 3-6, 6-3 win over Rohan Bopanna and Yasutaka Uchiyama.

 

The all-American teams of Jennifer Brady and Caroline Dolehide and Asia Muhammad and Sabrina Santamaria were also victorious in first-round action.

 

Six more Americans will be in singles action Thursday as the second round concludes.

 

No. 19 seed John Isner plays Chilean qualifier Alejandro Tabilo, and No. 29 seed Taylor Fritz plays two-time major finalist Kevin Anderson.

 

No. 26 seed Danielle Collins faces Yulia Putintseva of Kazakhstan; CiCi Bellis plays No. 20 seed Karolina Muchova of the Czech Republic; Lauren Davis meets fifth-seeded Elina Svitolina of Ukraine; and Townsend returns on short rest to play No. 30 seed Anastasia Pavlyuchenkova of Russia.