With the cancellation of last year’s Wimbledon, 2019’s defending gentlemen’s singles champion Novak Djokovic has waited two years for the privilege of opening play on the pristine grass of Centre Court.  Djokovic is playing for a lot of history this fortnight: he is halfway to a calendar Grand Slam, and is vying for his 20^th Major overall, which would tie him with both Roger Federer and Rafael Nadal.  Unfortunately, the defending ladies’ champion, Simona Halep, will miss her second straight Major due to a calf injury.  She is joined on the sidelines by Nadal, Naomi Osaka, and Dominic Thiem.

The top half of the men’s singles draw plays on Monday, featuring Djokovic, fellow Roland Garros finalist Stefanos Tsitsipas, and two-time Wimbledon champion Andy Murray.  Monday hosts the bottom half of the women’s draw, which includes eight Major singles champions.  Two of those Slam winners will meet in the opening round: two-time Wimbledon champion Petra Kvitova, and 2017 US Open champion Sloane Stephens.

Each day of the fortnight, this preview will highlight the five most intriguing matchups, while outlining the other notable matches on the schedule.   Monday’s play will begin at 11:00am local time on all outer courts, 1:00pm on No.1 Court, and 1:30pm on Centre Court

Aryna Sabalenka (2) vs. Monica Niculescu (Q) – 1:00pm on No.1 Court

Sabalenka has earned the second seeding based on her results outside the Majors, but the 23-year-old is yet to advance beyond the round of 16 at a Slam.  She’s just 1-3 lifetime at SW19, and went 2-2 this month in grass court lead-up events.  Niculsecu is a 33-year-old from Romania who reached the fourth round of The Championship in 2015, and has been ranked as high as No.28 in the world.  Monica is now barely inside the top 200, and started this season on an eight-match losing streak at all levels.  However, Niculescu won an ITF event on grass two years ago, and has won six grass court matches at all levels over the last two weeks.  Her unconventional style, which includes plenty of slice forehands, will serve as a fascinating contrast to the power game of Sabalenka.  Their only previous encounter occurred three years ago in Shenzhen, and went to Aryna in straight sets.  Sabalenka remains a slight favorite to prevail again today, though on this surface, Niculescu is a tricky first round draw.

Petra Kvitova (10) vs. Sloane Stephens – Second on Centre Court

This is a tough draw for both these players.  It’s hard to believe it was now 10 years ago when Kvitova won her first of two Wimbledon titles, while Stephens’ sole Major triumph came four years ago in New York.  Both women have overcome more than their fair share of struggles in recent years.  Kvitova’s comeback from an in-home invasion is one of tennis’ most inspiring stories, and just a few weeks ago at Roland Garros, she was forced to withdraw after injuring her ankle while walking down stairs on site.  Meanwhile, Stephens lost multiple members of her family this past year to COVID-19.  Sloane lost seven of her first eight matches in 2020, but gained some momentum this season with 11 wins on clay.  And she leads the head-to-head against Kvitova 2-1.  However, all three of those matches were contested on hard courts.  On the lawns of The All-England Club, the two-time champion’s lefty serve and forehand should enable her to even their head-to-head at 2-2.

Stefanos Tsitsipas (3) vs. Frances Tiafoe – Second on No.1 Court

This will be Tsistipas’ first match since his emotional loss to Djokovic in the French Open final, where he couldn’t close out the match despite winning the first two sets.  After the match, he revealed his grandmother had passed away just minutes before his first Major final.  It would be understandable if Stefanos is not 100% emotionally or physically just two weeks later, though he’s displayed his ability to bounce back quickly from devastating losses several times in his young career.  Tiafoe is a dangerous first round opponent.  The 24-year-old American won a Challenger title on grass earlier this month in Nottingham.  But he’s 0-2 against Tsitsipas, having yet to claim a set.  And notwithstanding the recent heartbreak Stefanos has endured, he is in the midst of a stellar season, with a record of 39-9.  He’ll likely secure his 40^th win on Monday.

Nikoloz Basilashvilli (24) vs. Andy Murray (WC) – Third on Centre Court

Since a hobbled Andy Murray lost in the 2017 Wimbledon quarterfinals to Sam Querrey, he’s only played 40 matches.  That was the last time Murray played a singles match at The Championships.  Multiple hip surgeries, as well as a groin injury and a positive COVID-19 test, have largely kept him off the court.  After defeating Benoit Paire in the opening round of Queen’s Club this month, Andy became quite emotional, as he described how thankful he is just to be competing again.  Monday will be his first time facing 29-year-old Basilashvilli, who can be an extremely streaky player.  Nikoloz has already earned two titles this season, yet has a losing record in 2021 outside of those two weeks.  He can bludgeon the ball, which leads to high winner and unforced error tallies.  Centre Court feels like home to Murray, and while he’s far from fully match tough, especially in the best-of-five format, he’ll be fully inspired to grit his way to victory.

Iga Swiatek (7) vs. Su-Wei Hsieh – Third on No.1 Court

This should be a highly entertaining affair between two of the sport’s most fun players to watch.  We have seen Swiatek excel on clay the last two seasons, but is the 20-year-old ready to succeed on grass?  She’s one of many younger players whose progress on grass has been impeded by the cancellation of all grass events last year.  Swiatek is only 0-1 at Wimbledon, and just 1-3 lifetime on this surface.  After winning the first set last week over Daria Kasatkina, she dropped 12 of the last 13 games to lose in three.  Hsieh is an unorthodox opponent who has made a name for herself by taking out top players at Majors.  In 2018, she upset Garbine Muguruza in Melbourne, and just six months later, defeated top-seeded Simona Halep on this very court.  At this year’s Australian Open, she achieved her first Major quarterfinal in singles.  But after that feat, she didn’t play for nearly three months, and has lost her last four matches.  Last October at Roland Garros, Iga beat Su-Wei in straight sets.  This surface could make today’s meeting much more complicated, but the eventual outcome should be the same considering Hsieh has not won a main-draw match since February.

Other Notable Matches on Monday:

Novak Djokovic (1) vs. Jack Draper (WC) – The five-time champ will be a heavy favorite against the 19-year-old British wild card, though it’s always worth watching the first match of the fortnight on Centre Court.

Alex de Minaur (15) vs. Sebastian Korda – De Minaur won the fifth title of his career just two days ago in Eastbourne.  20-year-old Korda is a strong American prospect who reached the quarterfinals of Halle with wins over Roberto Bautista Agut and Kei Nishikori.  This is the first of what will likely be many matches between these two rising stars.

Garbine Muguruza (11) vs. Fiona Ferro – The 2017 champion had a great start to this season before injuries set her back.  Ferro is a 24-year-old Frenchwoman who reached the second week of Roland Garros last fall.  Three years ago at the French, Muguruza defeated Ferro 6-4, 6-3.

Karolina Pliskova (8) vs. Tamara Zidansek – Pliskova is in a bit of a slump, with a 15-12 record in 2021, and an 0-2 record on grass.  Zidanzek was a surprising semifinalist a few weeks ago in Paris, who is just 2-2 lifetime on this surface.

Denis Shapovalov (10) vs. Philipp Kohlschreiber – Shapovalov is 1-3 thus far at Wimbledon, while the 37-year-old German was a quarterfinalist here nine years ago.  This is their first career meeting.

Sofia Kenin (4) vs. Xinyu Wang (Q) – The 2020 Australian Open champ has reached Major finals on both hard and clay courts.  She’s 2-2 at Wimbledon, though notably claimed a grass court title at the 2019 Mallorca Open.  Her opponent is a 19-year-old from China who has never won a match at a Slam.

Mihaela Buzarnescu vs. Venus Williams – Since the tour restart last summer, Venus is only 3-12, and is currently on a six-match losing streak.  A few weeks ago in Paris, Buzarnescu pushed her sister Serena to three sets.  And two years ago in Melbourne, Venus also overcame Buzarnescu in three sets.

Monday’s full Order of Play is here.