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Serena Williams will continue her quest for Grand Slam history on Monday as the top half contests the Round of 16. We’re previewing the matchups at WTATennis.com, courtesy of contributor Chris Oddo.

Monday

Round of 16

[1] Serena Williams (USA #1) vs. Yaroslava Shvedova (KAZ #52)
Head-to-head: Williams leads, 4-0
Key Stat: Williams is bidding to pass Roger Federer for the all-time lead in Grand Slam match wins on Saturday.

Serena Williams waltzed through the first week in New York, dropping a mere 15 games and proving to the field that her serve is on point. The shoulder is fine, the footwork is fine and the game is dialing in. Now, the 22-time major champion moves on to the business section of the draw. It starts with a fifth career meeting with hard-hitting Kazakh Yaroslava Shvedova. Williams has taken all four of the pair’s previous meetings, but one shouldn’t discount the talents of Shvedova. The World No.52 has won all six sets she’s played in New York to reach the second week at a major for the sixth time. She has the firepower to challenge Williams, but does she have the nerve? Approaching 35, and closing in on the all-time Open Era Grand Slam title record, Williams seems more motivated than ever to win. “I don’t know,” she said on Saturday after storming past Johanna Larsson of Sweden. “I just am not ready to throw in the towel yet or just to have enough yet. I’m still having fun out there. I’m still able to compete with the best. I think that’s what matters most for me.”

Pick: Williams in two

[4] Agnieszka Radwanska (POL #4) vs. Ana Konjuh (CRO #92)
Head-to-head: Radwanska leads, 1-0
Key Stat: Radwanska is one of four players to have reached the round of 16 at all four majors this year (along with Serena Williams, Keys and Suárez Navarro).

The last time Agnieszka Radwanska and Ana Konjuh locked horns, intense drama ensued. The pair battled into extra time in the second round at Wimbledon this year, with Radwanska saving three match points in the final set before winning, 6-2, 4-6, 9-7. Making the experience all the more painful for Konjuh was the fact that she turned her ankle after stepping on a ball at 7-7 in the decider and was severely hobbled at the finish. Less than two months later promising 18-year-old Konjuh has put the past behind her and raced into the round of 16 at a major for the first time in her career. On Monday the youngest player remaining in the draw gets to try to erase the memory of a Wimbledon gone awry. Can she possibly produce the type of tennis that earned her the three match points against Radwanska at the All England Club? Or will the No.4 seed have the perfect gameplan to ensure that Konjuh is kept at bay all day?

Pick: Radwanska in three

[5] Simona Halep (ROU #5) vs. [11] Carla Suárez Navarro (ESP #12)
Head-to-head: Tied, 5-5
Key Stat: Halep has won 20 of her last 22 matches.

Simona Halep really had to work to get past No.31-seeded Timea Babos on Day 6. Down a break in the third set and playing at a level or two below her best, Halep had to double-down on intensity and grind her way to a win. She did that, despite Babos’ inspired form, and lives to see another day in New York. “I don’t know how I came back,” a relieved Halep said on court after her 20^th hardcourt win of 2016. Will Halep’s narrow escape fuel her belief when she faces the proven veteran Carla Suárez Navarro for a spot in the quarterfinals? “Even if today I didn’t play my best, I played good tennis, good level,” said a confident Halep to reporters. “I was moving very well. I am happy to be back in the fourth round two years in a row, so it’s a good thing.” Halep and Suárez Navarro have gone the distance in each of their last three meetings, and they’ve split a total of ten matches since they first met in 2010. Who will break the tie on Monday?

Pick: Halep in three

[10] Karolina Pliskova (CZE #11) vs. [6] Venus Williams (USA #6)
Head-to-head: Williams leads, 1-0
Key Stat: The last time No. 6-seeded Williams was seeded this high in New York was 2010, when she was the No. 3 seed.

Finally, Karolina Pliskova has reached the second week of a major. The hard-serving Czech had been pining for the milestone ever since she emerged as a formidable force among the WTA’s elite at the start of 2015, but in the last two years she’s had nothing but hard luck at the majors. Not anymore. The 24-year-old surged past Anastasia Pavlyuchenkova on Saturday and will now set her sights on legendary Venus Williams in what promises to be scintillating round of 16 encounter. Two-time US Open champion Williams continued her fine showing in New York by blasting past Germany’s Laura Siegemund, 6-1, 6-2, on Saturday. The American defeated Pliskova in the Zhuhai final last year but Pliskova will likely carry more confidence into this tilt. She has won eight matches in a row, four of which came against members of the WTA’s Top 20.

Pick: Pliskova in three

By the Numbers:

36 – The age of Venus Williams, who is one of just three thirtysomethings (also Serena Williams and Robert Vinci) remaining in the draw.

3 – Radwanska is one of three players that could finish the tournament at No. 1 in the rankings, along with Serena Williams and Angelique Kerber. The Pole will need to win the title to become No. 1.

307 – Matches won by Serena Williams at majors. She’ll bid to pass Roger Federer’s all-time record of 307 on Day 8.

428 – Pliskova leads the Tour with 428 aces in 52 matches this year.

9 – Of the nine teenagers that started in this year’s US Open main draw, Konjuh is the only one remaining.

NEW YORK, NY, USA – World No.2 Angelique Kerber maintained her imperious form with a 6-3, 7-5 win over No.14 seed Petra Kvitova to reach the quarterfinals of the US Open.

Kvitova had held the early edge in their head-to-head, but Kerber had won their last two meetings to even the score, both this spring in Stuttgart and last fall at the BNP Paribas WTA Finals Singapore presented by SC Global. Playing textbook counterpuncher tennis throughout the evening, the German kept her stats clean with eight winners and just eight unforced errors.

Kvitova, by contrast, was far more aggressive, but her 32 winners couldn’t make up for the 43 unforced errors hit over two sets – 27 coming off her forehand side alone.

Giving it all you've got under the ??? of Ashe. #usopen pic.twitter.com/tBJOpp17t4

— US Open Tennis (@usopen) September 5, 2016

After trading breaks to start the contest, the match largely went with serve, including the first 11 games of the second set. Serving to force a tie-break, Kvitova ultimately succumbed on a double fault – her seventh of the night – allowing Kerber to wrap up th ematch in one hour and 28 minutes.

Up next for the reigning Australian Open champion is No.7 seed and 2015 US Open runner-up Roberta Vinci, who fought through a tough first set to defeat Lesia Tsurenko, 7-6(5), 6-2.

By reaching the quarterfinals, Kerber has put herself in even stronger position to leave the final major tournament of the season as World No.1 – the first from Germany since Stefanie Graf in 1997 – and prevent Serena Williams from breaking Graf’s record of consecutive weeks at the top spot. Serena is set to tie Graf’s record at 186, but now needs to do no worse than reach the final to have a chance of retaining World No.1.

Should Serena and Kerber meet in the final, the winner walks away with No.1.

She's looking for her third slam final this year and @AngeliqueKerber moves closer with a 6-3, 7-5 win over #Kvitova pic.twitter.com/5npAv1DWet

— US Open Tennis (@usopen) September 5, 2016

NEW YORK, NY, USA – Two-time US Open finalist Caroline Wozniacki has tapped into some New York magic once more, taking out No.8 seed Madison Keys, 6-3, 6-4, to reach her first Grand Slam quarterfinal in exactly two years.

“It’s been a good week,” Wozniacki said after the match. “I’m really happy about the way I played. Obviously Madison is a strong player. She hits the ball really hard.

“But I managed to really play well, get a lot of returns in. I served well, which I was pleased with.”

Dealing with injuries throughout the 2016 season, the former No.1 had tumbled all the way down to No.74 in the rankings, but is set to begin her climb back in earnest thanks another big win in Flushing. Playing Keys for the first time, the Dane relied on her signature consistency to frustrate the young American, winning 80% of her first serve points and hitting just three unforced errors in the one hour and 18 minute match.

“Everybody wants to beat you. No matter what my ranking is at this current moment , I always feel like I’m a target. I have to keep improving to beat everybody. I feel like I have been serving well this week, especially today, and returning well and really having good court coverage.”

Two-time #usopen finalist #Wozniacki off to a hot start against Madison #Keys, taking the opener 6-3. @chase https://t.co/CTc5svPzwB

— US Open Tennis (@usopen) September 4, 2016

Keys had come off a hard-fought third round win against fellow young gun Naomi Osaka, and despite hitting 30 winners against Wozniacki, 33 unforced errors proved critical on Sunday, engineering just one break point all day.

“I definitely felt like I got off to a bad start, and then I felt like I was trying to catch up from there,” Keys said in her post-match press conference.

“I definitely don’t think I was playing my best. I mean, I think she played really, really well today. I think it was just a combination of me not playing my best and not playing super smart and her playing really well.

“I feel like the match just got away from me.”

Up next for Wozniacki is comeback kid Anastasija Sevastova, who continued her own Cinderella run into the quarterfinals with a 6-4, 7-5 win over No.13 seed, Johanna Konta.

“I had some tough matches against her in the past,” Wozniacki said. “I think we played Fed Cup a couple of times, but also we played the Australian Open.

“She’s a tough player. She’s a tough opponent. She has a lot of grit and good hands. It’s not going to be an easy one, but I’m excited just to have another shot.”

Calm and relaxed throughout the fortnight, Wozniacki even took in some of Saturday night’s match between Stan Wawrinka and Dan Evans, trying her hand at providing match analysis on Twitter:

What a match happening on Armstrong now!! Will be interesting to see how Evans will bounce back for the 5th set after having had match point

— Caroline Wozniacki (@CaroWozniacki) September 4, 2016

NEW YORK, NY, USA – Martina Hingis and CoCo Vandeweghe continued to strengthen their fledgling partnership with a hard-fought win over Xu Yifan and Zheng Saisai at the US Open on Sunday.

As in the previous two rounds, Hingis and Vandeweghe did not have things all their own way, coming from a break down in the final set to see off their Chinese opponents, 6-4, 4-6, 6-2, in a little over two hours.

“It was an early break so we knew we had a whole set to play. Obviously after losing the second [set] it wasn’t the greatest situation,” Hingis said about their rousing finish. “I mean, they played really well in that first game too – they kept it away from me and made a lot of returns on CoCo’s serve.”

The No.6 seeds looked well set for a smooth passage into the quarterfinals when they took the first set and then moved 3-1 ahead in the second. “I think it was more frustrating to lose the second set because it was kind of there for us to take it,” Hingis added. “But, I mean, this happens, and it’s not a surprise for a tennis player to be broken in the first game after losing the momentum.

“But we were right back on it and I think that was the key; we broke them right back and then won a couple of tight games.”

Vandeweghe is playing only her second event alongside Hingis – they teamed up to reach the final in Cincinnati – and admits the unison was not an expected one: “I got a call from and unusual number and the only reason I answered it – because I usually don’t pick up numbers I don’t know – was that it was such a bizarre number, plus whatever, so I knew it had to be some tennis player!

“I was just at home and Martina asked if I wanted to play Cincinnati and US Open. I told her that I already had two partners but let me think about it, and I almost felt a little big headed for telling her, ‘Let me think about it’. I told my coach and he told me I was crazy to even think about it. I just enjoyed my time at home to let her sweat it out before calling back!”

Also advancing were a couple of more established pairs, including top seeds Caroline Garcia and Kristina Mladenovic, who had few problems defeating Eri Hozumi and Miyu Kato, 6-2, 6-3. No.5 seeds and recent Olympic champions Ekaterina Makarova and Elena Vesnina were made to work somewhat harder, fighting back to defeat Vania King and Monica Niculescu, 2-6, 6-1, 6-2.

Another team battling back from a slow start were wildcards Asia Muhammad and Taylor Townsend. Taking on No.3 seeds Timea babos and Yaroslava Shvedova, the young Americans looked well out of their depth for the opening 20 minutes only to produce a stunning turnaround to eventually triumph, 0-6, 6-4, 6-3.

The decisive moment came at 3-3 in the final set, Muhammad and Townsend harnessing the energy of a partisan crowd to break in a marathon game before repeating the trick a few games later to complete the unlikely upset. Their reward is a meeting with compatriot Bethanie Mattek-Sands and her partner Lucie Safarova, after they saw off No.8 seeds Julia Goerges and Karolina Pliskova, 2-6, 7-5, 6-3.

NEW YORK, NY, USA – Week 1 is in the books at the US Open, and catch up with all the best moments on Day 6’s Daily Dispatch from the WTA Insider Podcast.

Save for a three-set struggle from No.5 seed Simona Halep, all the big names progressed into the second week with relative ease on Saturday, include World No.1 Serena Williams, No.4 seed Agnieszka Radwanska, No.6 seed Venus Williams, and No.10 seed Karolina Pliskova, who reached the fourth round at a major for the first time in her young career.

Analyzing the week that was, the WTA Insider team looks ahead to Day 7, and whether there might be an upset or two on the table come Sunday.

Subscribe to the podcast on iTunes, Stitcher, TuneIn or on any podcast app of your choice to ensure you never miss an episode when they go live. Reviews are always helpful, so if you like what you’ve heard so far, leave us one. You can also get new episode alerts by following us on Twitter @WTA_Insider.

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NEW YORK, NY, USA – A battle of elite southpaws highlights the Day 7 schedule in New York. We preview Sunday’s Round of 16 tilts at wtatennis.com.

Sunday
Round of 16

[2] Angelique Kerber (GER #2) vs. [14] Petra Kvitova (CZE #16)
Head-to-head: Tied, 4-4
Key Stat: Kerber will ascend to the No.1 ranking if Serena Williams does not reach the semifinals in New York.

Two talented southpaws and former Grand Slam champions will meet in one of the most heavily anticipated matches of the tournament on Day 7. Angelique Kerber is in hot pursuit of the No.1 ranking and she has been fit and focused in New York, dropping just ten games in three rounds. But Sunday’s task promises to be far more daunting than her first three challenges. Kerber will have to square off against a menacing lefty who is finally learning how to excel at the US Open. Kerber has faced Petra Kvitova eight times before, with the pair splitting the pot, but never have they met at a Grand Slam. “Playing against lefties is always a little bit different,” Kerber said on Friday after racing past 17-year-old American CiCi Bellis, 6-1, 6-1. “I played a lot of matches against Petra and we had great matches in the past, so I think it will be a good match. I will try to go for it, go out there to win the match.” Kerber has won 15 of 18 this hardcourt season and has every reason to like her chances on Sunday. “I’m confident. I will go out there and try to enjoy every moment here,” she said. But Kvitova is a confident player herself. A quarterfinalist for the first time at the US Open last season, Kvitova says she is finally starting to understand how to harness the energy of the Big Apple. “I feel that the crowd, it’s always, you know, cheering,” she said after defeating Elina Svitolina on Day 5. “I think finally I find the way how I should take the energy from them as well.”

Pick: Kvitova in three

[7] Roberta Vinci (ITA #8) vs. Lesia Tsurenko (UKR #99)
Head-to-head: Vinci leads, 1-0
Key Stat: Tsurenko is the lowest-ranked player left in the draw.

Roberta Vinci has been here before. The Italian who stunned Serena Williams in last year’s semifinals clearly is having a love affair with the US Open and it shows in the form of nine wins in her last ten matches in Queens. Lesia Tsurenko, on the other hand, is into uncharted waters. The Ukrainian reached the second week of a major for the first time on Friday when she shocked No.12-seeded Dominika Cibulkova in three sets. Tsurenko, playing at her lowest ranking in two years, entered the event with a four-match losing streak at majors and a lifetime 8-20 record at the Grand Slam level. But she’s a battler, and she has five career Top 10 wins to her name as well. But can Tsurenko take the play to an in-form Vinci that is playing her best tennis of the season? The Italian had only won five of her last 15 heading into New York, but she is clearly resonating with the place of her greatest Grand Slam achievement.

Pick: Vinci in two

[8] Madison Keys (USA #9) vs. Caroline Wozniacki (DEN #74)
Head-to-head: First meeting
Key Stat: Keys owns a 14-4 record in three-setters in 2016.

Fresh off the greatest comeback of her young career, 21-year-old American Madison Keys will set her sights on reaching the US Open quarterfinals for the first time. But standing in her way is a suddenly resurgent two-time US Open runner-up who has always thrived in New York. Caroline Wozniacki is finally finding her form after a long and unspectacular season, and she will be a very dangerous opponent for the No.8-seeded Keys. But Keys is confident and feeling lucky after narrowly escaping defeat in two of her first three matches. “I think the biggest thing is I’m never giving up and I’m fighting to the very end,” Keys said after battling back from 5-1 down in the third set to defeat Japan’s Naomi Osaka on Day 5. “That’s something to pat myself on the back for.” Wozniacki has had to fight through her fair share of injuries in 2016, but she’s hoping it’s all behind her. “Every time I have come back something else has been hurting,” she said. “Knock on wood, right now I’m feeling good.” Does she feel good enough to deconstruct Keys’ lethal game or will it be the young American who moves on?

Pick: Keys in three

[13] Johanna Konta (GBR #14) vs. Anastasija Sevastova (LAT #48)
Head-to-head: Konta leads, 1-0
Key Stat: Konta owns a 27-10 hardcourt record in 2016.

The first British player to hold a Top 20 ranking in nearly 30 years will take a shot at reaching her first US Open quarterfinal on Sunday against an unlikely opponent. Johanna Konta and Anastasija Sevastova will meet for the first time in a main draw and the second time overall. Konta will be the favorite based on her higher ranking and impressive hardcourt record this season, but Sevastova is putting the cherry on top of a solid season by making her first run to the second week of a major in over five years. The Latvian No.1 shocked Garbiñe Muguruza on Day 3 and on Friday she won for the first time in four meetings against Kateryna Bondarenko. Konta, who nearly had to retire due to heat-related exhaustion in her second round win over Tsvetana Pironkova, rebounded smartly on Friday by trouncing Belinda Bencic, 6-2, 6-1. Having recovered fully, Konta looks set to make another deep run at a hardcourt major. Is there anything Sevastova can do to stop her?

Pick: Konta in three

By the Numbers:
1-0 – Wozniacki’s record against the Top 10 this season. The Dane defeated No.10 Svetlana Kuznetsova in the second round.
36-11 – Kvitova’s career record against left-handers. Kerber’s career record against lefties is 26-15.
1 – Number of players in Top 10 to have yet to play in a Grand Slam final (Madison Keys).