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WIMBLEDON—A common activity for those visiting London is to head to the theatre district and take in a play. But if it's drama theatergoers seek, they ought to head to the southwest portion of the city—particularly this Sunday afternoon, for an exceptionally see-saw-like round-of-16 match between seventh-seeded Jasmine Paolini and 12th-seeded Madison Keys.

The plot spoiler here is that this tussle on No. 1 Court ended in a way that couldn’t help but make one feel sorry for both players. With Paolini serving at 5-5, 15-all in the third set, Keys limped forward to retire due to a left thigh injury that had cropped up earlier.

Upon that mutually frustrating conclusion, Paolini advanced to her second consecutive Grand Slam quarterfinal. Remarkably, as recently as last December, Paolini had only won four singles matches in 16 Grand Slam tournaments. But in 2024, she’s gone to the round of 16 at the Australian Open, the final of Roland Garros and, now, the last eight at Wimbledon.

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“It's a little bit also strange to be in this position because I never been in this position,” said Paolini. “I always thought it would be great to be in this position. Now I'm here winning more matches this year. It feels great. I'm enjoying, as I said. It's important to me to enjoy every moment because, as I said, it's a dream.”

Keys had served for the match twice. The first opportunity came at 5-2. Serving at 30-all and again at deuce, Keys was unable to close off the tenacious Paolini. The last point of that game was when Keys’ injury first surfaced. Upon missing an inside-in forehand, she flexed her left leg. This initially seemed mild.

Keys took a medical timeout, but things would only grow more dire.

Keys took a medical timeout, but things would only grow more dire.

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But following a Paolini hold, Keys took the rare step of calling for the trainer and even leaving the court prior to her second attempt to close things out. Upon return, Keys wore tape on her left thigh, at which point the injury began to appear far more serious.

On the first point of the 5-4 game, Keys attempted to bail out of the rally with a drop shot. Paolini won that point. More notably, with Keys unable to push off her left leg, her second serve became a shadow of itself. At 15-30, a second serve clocked in at only 76 MPH, followed by another at 74 MPH, and then, at 30-40, a double-fault.

And though Keys won the first point of the 5-5 game courtesy of a clever drop shot-lob sequence, an ace from Paolini at 0-15 proved conclusive. After two hours and 23 minutes, Paolini had won, 6-3, 6-7 (6), 5-5, 15-all, retired.

“I was trying to fight every point because you never know here on grass if you are up or if you are down, every match can I think turn, you know, turn around,” said Paolini. “I was, like, just be focus and try to win points, to play points by point.”

Keys couldn't hide her emotions as the match came to its inevitable conclusion.

Keys couldn't hide her emotions as the match came to its inevitable conclusion.

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But don’t think the drama was only confined to those final stages.

“It was a rollercoaster,” said Paolini in her post-match on-court interview.

Early on, the Italian had thoroughly dictated the tempo of just about every rally, requiring a mere 16 minutes to take a 4-0 first set lead and soon enough capture it, 6-3. Repeatedly, Keys lined backhands into the net and proved unable to dictate much of anything versus the enterprising and attentive Paolini. When Paolini broke Keys to start the second set, all seemed on course.

Then came a twist. Keys began to find her range. This was Keys at her best, a smothering flurry of depth, pace and accuracy that saw her race through five straight games and appear on the way to swiftly taking the match into a third set.

“Yeah, was a roller coaster because I think she's playing unbelievable,” said Paolini. “I was doing more mistakes, her level was going up. It's not easy to play against her because I think she's one of the best players in the world. Of course, she's hitting so fast.”

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Not quite. Serving at 5-1, 40-15, Keys double-faulted, lost her second set point to a sharp Paolini volley, and subsequently surrendered her serve. Now it was Paolini’s turn to rally.

Off she went, rapidly evening the set at 5-all. Soon enough came a tiebreaker and the highest quality tennis of the match, each player upping her level of power and movement. With Paolini serving at 6-7, Keys improvised her way to parity, courtesy of a sublime backhand half-volley that set up a rally-closing backhand volley winner.

Alas, there was not a clue then of how a simple conflict story would eventually end in tragedy. Unlike what happens in London’s theatre district, tennis matches are unscripted.