On Wednesday, for the first time in history, three WTA 500 tournaments will play out at a single venue.

The world’s six top-ranked players – Ashleigh Barty, Simona Halep, Naomi Osaka, Sofia Kenin, Elina Svitolina and Karolina Pliskova – all are in action in the Yarra Valley Classic and Gipsland Trophy events on the crowded grounds of Melbourne Park.

Oh, and did we mention Serena Williams?

And if that’s not enough to induce a prolonged bout of binge-watching, how about a dozen bonus singles matches featuring the unlucky players strictly confined to their rooms for two weeks of quarantine? Yes, the Grampians Trophy rolls out with a field that includes former Grand Slam champions Angelique Kerber, Victoria Azarenka, Svetlana Kuznetsova and Sloane Stephens.

On to the myriad matches:

Yarra Valley Classic

No. 5 Serena Williams vs. Tsvetana Pironkova

Playing her first WTA match since pulling out of the French Open with an Achilles injury, Serena looked sharp in her first-round win against Daria Gavrilova. Now Williams faces the very player she sent into the third round at Roland Garros.

These two, as they say, have a history. They are both 30-something mothers; Serena has a 3-year-old daughter, Olympia, and Pironkova’s son, Alexander, turns 3 in March. And, oddly enough, they also met in the quarterfinals of the 2020 US Open, when Pirokova won the first set and Serena had to scramble to a three-set victory.

“It’s important for me just to see what she did and what I did and what we can both do better,” Serena said Monday, sounding like she was headed to the videotape. “I’m always rooting for her, she’s like such a great story.”

Photo by Getty Images

Indeed, Pironkova sat out the 2018 and 2019 seasons only to return in 2020 for appearances opposite Williams in the season’s last two majors.

Serena has won all five of their meetings (not including that walkover), but three of those matches went to three sets.

The Bulgarian upset No. 9 seed Donna Vekic to reach this third-round match.

No. 1 Ashleigh Barty vs. No. 16 Marie Bouzkova

It’s been more than 11 months since Barty played a WTA match, and Tuesday the Australian immediately launched into vintage form. She dispatched Ana Bogdan 6-3, 6-3 to advance to the third round.

Afterward, Barty said her offseason work with coach Craig Tyzzer paid immediate dividends. 

“I thought it was brilliant,” she said. “I thought I was able to stick to the idea of what we wanted to do, stick to our game plan of what we wanted to do tonight to try and dissect Ana’s game as best as we could. I thought it was solid throughout the whole night.”

Bouzkova, a 21-year-old Czech, had some nice results in 2020, reaching the final at Monterrey. She defeated Aliona Bolsova in three sets to get here.

These two have never met.

No. 3 Karolina Pliskova vs. No. 13 Danielle Collins

Pliskova has never played Collins, but clearly the American’s reputation Down Under precedes her.

Asked about her third-round opponent, Pliskova offered this: “She’s playing well here always, every year. It’s going to be an interesting.”

Bet on it. Collins is a Floridian, but she might consider calling Australia her second home. Her best Grand Slam result came in Melbourne, the semifinals in 2019, where she lost to Petra Kvitova. Last year’s summer swing was outstanding as she went 2-1 in Brisbane (beating Elina Svitolina in the first round), reached the semifinals in Adelaide (ousting Sofia Kenin and Belinda Bencic in the process) and reached the second round of the Australian Open.

Collins hasn’t dropped a set in two matches, while Pliskova handles Italian Elisabetta Cocciaretto in her third match of the new year.

“It was a good start,” she said afterward. “When you have not many matches, maybe you are thinking too much.”

Of note

No. 2 Sofia Kenin vs. Jessica Pegula: Kenin has an eight-match winning streak at Melbourne Park; No. 6 Garbiñe Muguruza vs. No. 11 Anastasia Pavlyuchenkova: Muguruza won her third match of the young season, 6-2, 6-0 over Alison Van Uytvanck; No. 4 Petra Kvitova vs. No. 14 Nadia Podoroska: Kvitova defeated Venus Williams 7-6 (6), 7-5, her first win over the 40-year-old American in nearly seven years.

Gippsland Trophy

No. 2 Naomi Osaka vs. Katie Boulter

Predictably, Osaka took care of Alize Cornet, 6-2, 6-2, her first WTA match since winning the US Open last fall. What wasn’t predicted was her opponent.

Boulter, ranked No. 371 after a sabbatical induced by a spinal stress fracture, stunned No. 14 seed Cori Gauff 3-6, 7-5, 6-2.

A year ago, the American teenager shocked Osaka, the defending Australian Open champion, in a straight-sets third-round victory. So, instead of Gauff, the three-time Grand Slam champion faces Boulter, whose previous three outings were in ITF events last fall.

“Actually I was nervous the entire match,” Osaka said. “Even until the very last point, I think I was just thinking - I don’t know, the first match you come back and especially in a Grand Slam environment, it’s definitely very hard.”

Boulter, a 24-year-old from Great Britain, lost twice to Osaka, at Birmingham and Wimbledon, in 2018.

No. 1 Simona Halep vs. No. 16 Laura Siegemund

After defeating Anastasia Potapova 6-4, 6-4 on Monday, Simona Halep said, “I needed this victory, because I didn’t play an official match since October of last year, so it’s been a long time.” 

She was referring to the French Open where she was surprised by eventual champion Iga Swiatek in the fourth round. Halep won three games in that match.

Believe it or not, her Wednesday opponent got one round further in Paris. Siegemund had her best Grand Slam result ever -- at the age of 32 -- losing to Petra Kvitova in the quarterfinals.

Another fun fact: Siegemund actually holds a 2-1 head-to-head advantage over Halep, with wins in Stuttgart in 2016 and 2017.

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No. 3 Elina Svitolina vs. No. 13 Jelena Ostapenko

Ostapenko holds a 2-1 edge in the head-to-head, but Svitolina won the last one, in Doha, 2019.

Svitolina advanced with a second-round win over veteran Andrea Petkovic and had previously reached the quarterfinals at Abu Dhabi.

Ostapenko, playing her first matches since last October, advanced to the third round by defeating Sara Errani and Danka Kovinic. The 2017 French Open champion is ranked No. 45.

Of note

No. 5 Iga Swiatek vs. No. 9 Ekaterina Alexandrova

Grampians Trophy

Bianca Andreescu was set to play her first match in 15 months as the top seed here. But after 14 days of a lock-down quarantine and a few days of practice, she decided she wasn’t quite ready.

As a result, the top seed will be Maria Sakkari, with Victoria Azarenka, Belinda Bencic and Elena Rybakina also receiving byes.

No. 8 Angelique Kerber vs. Katerina Siniakova: The former world No. 1 reached the fourth round at both the 2020 Australian Open and US Open.

No. 7 Jennifer Brady vs. Svetlana Kuznetsova: The 25-year-old American got to the semifinals of last year’s US Open; Kuznetsova won the 2004 US Open.

Sloane Stephens vs. Leylah Fernandez: The 2017 US Open champion meets the up-and-coming 18-year-old Canadian. 

ORDER OF PLAY

MARGARET COURT ARENA - Starts at: 11:00 AM
Gippsland Trophy - BOULTER, Katie (GBR) vs. OSAKA, Naomi (JPN) [2] 
Yarra Valley Classic - BARTY, Ashleigh (AUS) [1] vs. BOUZKOVA Marie (CZE) [16]
Gippsland Trophy - HALEP, Simona (ROU) [1] vs. SIEGEMUND, Laura (GER) [16]

MARGARET COURT ARENA - Not before: 6:30 PM
Yarra Valley Classic - PIRONKOVA, Tsvetana (BUL) vs. WILLIAMS, Serena (USA) [5]
Yarra Valley Classic - PLISKOVA, Karolina (CZE) [3] vs. COLLINS, Danielle (USA) [13] 

1573 ARENA - Starts at: 11:00 AM
Gippsland Trophy - OSTAPENKO, Jelena (LAT) [13] vs. SVITOLINA, Elina (UKR) [3]
Yarra Valley Classic - PEGULA, Jessica (USA) vs. KENIN, Sofia (USA) [2] 

COURT 5 - Starts at: 10:30 AM
Grampians Trophy - DABROWSKI, Gabriela (CAN) vs. KOSTYUK, Marta (UKR)
Grampians Trophy - JABEUR, Ons (TUN) vs. BLINKOVA, Anna (RUS)
Grampians Trophy - CIRSTEA, Sorana (ROU) vs. KALASHNIKOVA, Oksana (GEO)
Grampians Trophy - PEREZ, Ellen (AUS) vs. LI, Ann (USA)
Grampians Trophy - DAVIS, Lauren (USA) vs. KREJCIKOVA, Barbora (CZE)
Grampians Trophy - PUTINTSEVA, Yulia (KAZ) vs. GARCIA PEREZ, Georgina (ESP)

COURT 7 - Starts at: 10:30 AM
Gippsland Trophy - MERTENS, Elise (BEL) [7] vs. GARCIA, Caroline (FRA) [12]
Gippsland Trophy - KONTA, Johanna (GBR) [5] vs. BEGU, Irina-Camelia (ROU)
Gippsland Trophy - PAOLINI, Jasmine (ITA) vs. MUCHOVA, Karolina (CZE) [8] 
Gippsland Trophy - KANEPI, Kaia (EST) vs. KASATKINA, Daria (RUS)
Yarra Valley Classic - PODOROSKA, Nadia (ARG) [14] vs. KVITOVA, Petra (CZE) [4]
Gippsland Trophy - JURAK, Darija (CRO) / STOJANOVIC, Nina (SRB) vs. CHAN, Hao-Ching (TPE) / CHAN, Latisha (TPE) [2]

COURT 8 - Starts at: 10:30 AM
Grampians Trophy - STRYCOVA, Barbora (CZE) vs. MATTEK-SANDS, Bethanie (USA)
Grampians Trophy - MCHALE, Christina (USA) vs. KONTAVEIT, Anett (EST) [6]
Grampians Trophy - BRADY, Jennifer (USA) [7] vs. KUZNETSOVA, Svetlana (RUS)
Grampians Trophy - WATSON, Heather (GBR) vs. KUDERMETOVA, Veronika (RUS)
Grampians Trophy - SINIAKOVA, Katerina (CZE) vs. KERBER, Angelique (GER) [8]
Grampians Trophy - FERNANDEZ, Leylah (CAN) vs. STEPHENS, Sloane (USA)

COURT 10 - Starts at: 10:30 AM
Following 2 ATP matches
Yarra Valley Classic - SASNOVICH, Aliaksandra (BLR)/KOSTYUK, Marta (UKR) vs. XU, Yifan (CHN) / YANG, Zhaoxuan (CHN) [6]
Gippsland Trophy - DABROWSKI, Gabriela (CAN) / MATTEK-SANDS, Bethanie (USA) [3] vs. GAVRILOVA, Daria (AUS) / HALEP, Simona (ROU)
Yarra Valley Classic - BARTY, Ashleigh (AUS) / BRADY, Jennifer (USA) [8] vs. JABEUR, Ons (TUN) /MCHALE, Christina (USA)
Gippsland Trophy - BLINKOVA, Anna (RUS) / KUDERMETOVA, Veronika (RUS) [8] vs. MYERS, Abbie (AUS) / POPOVIC, Ivana (AUS)

COURT 13 - Starts at: 10:30 AM
Yarra Valley Classic - ROGERS, Shelby (USA) vs. MARTIC, Petra (CRO) [7]
Yarra Valley Classic - VONDROUSOVA, Marketa (CZE) [8] vs. ZVONAREVA, Vera (RUS)
Gippsland Trophy - ALEXANDROVA, Ekaterina (RUS) [9] vs. SWIATEK, Iga (POL) [6]
Yarra Valley Classic - MUGURUZA, Garbiñe (ESP) [6] vs. PAVLYUCHENKOVA, Anastasia (RUS) [11]
Yarra Valley Classic - GAUFF, Coco (USA) / MCNALLY, Catherine (USA) vs. MUCHOVA, Karolina (CZE) / VONDROUSOVA, Marketa (CZE)
Gippsland Trophy - RODIONOVA, Arina (AUS) / SANDERS, Storm (AUS) vs. BOUZKOVA, Marie (CZE) / SORRIBES TORMO, Sara (ESP)