Grigor Dimitrov and the Long Way Back to Cincinnati

The last time Grigor Dimitrov was the biggest story in tennis, he was lying on the grass at Wimbledon with one hand pressed to his chest, and the man he was beating was climbing over the net to help him up.

You probably remember the pictures even if you were only half watching. July 2025, fourth round, Centre Court. Dimitrov led Jannik Sinner by two sets to love — 6-3, 7-5 — and was level at 2-2 in the third. He hit an ace. Then he crumpled. A partially torn pectoral muscle, the kind of injury that arrives without warning and ends everything in the space of one serve. Sinner crossed to his side of the court, checked on him, and then carried Dimitrov's bags off court for him, the world number one turned porter because there was nothing else useful a person could do.

That was the fifth Grand Slam in a row that Dimitrov had been unable to finish. It also cost him the US Open, which ended a run of 58 consecutive Grand Slam appearances stretching back to the 2011 Australian Open. Fourteen years of always being there, gone in a single afternoon.

This week he is in Ohio, at the Cincinnati Open, playing on a wild card. He is 35 years old and ranked outside the top 100. And the peculiar, lovely thing about this particular tournament is that it is the same one he won.

The most beautiful game nobody could quite explain

If you have followed tennis for any length of time, you have an opinion about Grigor Dimitrov, and the opinion is probably tangled up with a nickname he never asked for.

They called him Baby Federer. It was meant as the highest compliment available in the sport, and for years it functioned as something closer to a curse. He had the one-handed backhand, the loose shoulders, the way of arriving at the ball early and unhurried so that a difficult shot looked like a decision rather than a scramble. Watch old clips and you will see it: the pause at the top of the ball toss, the whip of the racket head, the sense that this was a player who had studied beauty and then gone out and learned it.

The problem with being told you resemble the greatest stylist the game ever produced is that everybody then waits for you to produce his results. When you do not, the compliment curdles. For most of his twenties, Dimitrov was written about as a disappointment — a player of enormous gifts who kept losing matches he ought to have won, who could take a set off anyone and then lose the plot in the third.

That is a brutal way to be discussed in public for a decade. It is also, on the evidence, not really true. Three Grand Slam semi-finals is not a failure. Beating a defending champion at Wimbledon is not a failure. But tennis has a habit of measuring people against the ceiling somebody else imagined for them, and Dimitrov spent years being measured against a ceiling he had never claimed.

The autumn when everything worked

Then came 2017, and for about three months Grigor Dimitrov was the best story in men's tennis.

In August of that year he arrived in Cincinnati and did not lose a set all week. Not one. In the final he beat Nick Kyrgios 6-3, 7-5 — Kyrgios at his most dangerous, all serve and improvisation — and Dimitrov simply refused to blink. It was his first Masters 1000 title and his third trophy of the season.

If the story had stopped there it would already have been the best year of his life. It did not stop there. In November he qualified for the season-ending ATP Finals in London as a debutant, went through the round robin, and beat David Goffin in the final 7-5, 4-6, 6-3 to win the biggest indoor title in the sport. No debutant had won it since Alex Corretja in 1998. He finished the year at world number three, behind only Rafael Nadal and Roger Federer, which is a sentence you would like to have on your gravestone if you play tennis for a living.

The Cincinnati crowd have a long memory for that fortnight, and so does he. Nine years is a long time in an athlete's life, but the O2 trophy and the Cincinnati trophy are on the same shelf, and it turns out the Cincinnati one is the easier of the two to go back and visit. He has been given a wild card into this year's main draw alongside Stan Wawrinka, Gael Monfils and Jack Draper — four men whose combined highlight reel would keep you up until three in the morning. If you want the background on why this event carries the weight it does in the American summer, our guide to the Cincinnati Masters walks through the history.

He has done this before

It is worth remembering, before we get to the difficult years, that resurrection is something of a Dimitrov speciality.

By the summer of 2019 he had slid out of the top 70 and the obituaries were already being drafted. He arrived in New York ranked 78th in the world, which at the US Open puts you in the section of the draw nobody bothers to preview. He then beat Roger Federer in the quarter-finals — Federer, in New York, in five sets — and walked into a Grand Slam semi-final as the second-lowest-ranked man ever to reach that stage at the tournament. He lost the semi-final, and he lost it well.

Nobody saw that coming, least of all the people who had spent the previous eighteen months explaining that he was finished. It is the single most useful thing to know about him: his career has never moved in a straight line, and the flat stretches have a habit of ending abruptly and without notice.

What the ranking cannot tell you

Here is the part of the story that fans tend to skip, because it is unglamorous and slow and there are no highlights of it.

Coming back from a torn pectoral is not a matter of waiting for the muscle to knit and then resuming your career. Dimitrov started 2026 in Brisbane and lost, and lost again, and kept losing. In April, after an early exit in Monte Carlo, he dropped out of the world's top 100 for the first time in fourteen years. Consider what that actually means: a man who had been a top-100 player continuously since he was 21 was suddenly not one. He went back to the Challenger circuit — the second tier, small crowds, long drives, no ball kids in some places — and lost to a player ranked 312th in the world.

At his lowest point this year he was outside the world's top 150, and for a while outside 160. He was asked about it before Wimbledon and did not perform the usual athlete's serenity. "The way our ranking is structured is so unfair that it makes no sense to talk about it," he said. "It is simple: if you win, you have a high ranking. If you lose, you keep dropping in the rankings." You can hear the frustration of a man who understands the arithmetic perfectly well and resents having to explain it.

What he said about the injury itself was more revealing, and if you have ever come back from anything — surgery, illness, a bad year — you will recognise it immediately. He talked about being frightened. "I was frightened of the thought of having to come back on the court again and start hitting," he said. "My first hits, even practices, were extremely difficult for me mentally to not only swing through, but I had lots of flashbacks, and it was just a very, very uncomfortable feeling." And: "You start questioning everything and you start doubting everything."

He also described what happened immediately after Sinner walked him off Centre Court. "I cried for two hours in the locker room, came out straight to the hospital, and I was like, OK, good, now the rehab starts."

Two hours, and then the practical sentence. That is a very particular kind of toughness, and it is not the kind that shows up in a stat sheet. The physical side of these comebacks is only ever half the job — we have written before about how tennis players recover from serious injuries, and the recurring theme is that the body is usually ready before the nerve is.

Centre Court, again

Wimbledon gave him a wild card this summer. He was ranked 146th and it was, frankly, a sentimental decision as much as a sporting one. It turned out to be the best call the All England Club made all fortnight.

He beat the Australian Dane Sweeny in the first round. Then he beat the 15th seed Jakub Mensik — one of the hardest hitters of the new generation — 7-6(5), 4-6, 7-5, 6-3, which is not a scoreline you produce by nostalgia. And then, in the third round, he was sent back out to Centre Court. The same court. Twelve months on.

His opponent was Matteo Berrettini, himself a Wimbledon finalist and himself a man who has spent years fighting his own body. They played for the better part of four hours and Dimitrov won it 6-3, 6-4, 3-6, 5-7, 6-3, losing a two-set lead and then, this time, refusing to let the match go with it. Anyone who watched knew exactly what the fifth set was about. It was about the last time he had been ahead by two sets on that piece of grass.

It carried him into the fourth round for the sixth time in his career. And then, because tennis has a novelist's sense of cruelty, he lost a match he was winning. Arthur Fery — a British wild card ranked far below him, a player almost nobody outside the country had heard of a month earlier — came back from two sets to one down and beat him 7-5, 3-6, 4-6, 6-4, 7-6(7) in three hours and 55 minutes. A fifth-set tiebreak. Seven points to five in the breaker. Fery went to the quarter-finals and became the story of the summer in Britain; if you missed how that unfolded, the tale of the wild card who grew up ten minutes from Wimbledon is worth your time.

For Dimitrov, though, it was the strangest possible result: the best fortnight he had produced in two years, ending in a loss from a winning position, on the court where the last winning position had ended in an ambulance. He walked off to a standing ovation.

Why any of this should matter to you

There is a version of the tennis calendar that only really cares about four or five people. Sinner and Alcaraz are both missing Cincinnati this year with a knee and a wrist, which has thrown the men's draw wide open and handed the top seeding to Alexander Zverev, chasing form in Ohio before New York. That is the headline. That is what the previews are about.

But the reason people fall in love with this sport is rarely the headline. It is a specific human being walking out alone with a bag over one shoulder, no substitutions available, no team-mate to hide behind, and finding out in public whether the work held.

Dimitrov's first-round opponent here is the Argentine Sebastian Baez, a fine hard-court test and no gift of a draw. The tournament runs to 23 August, the US Open follows in New York, and the realistic ceiling for a 35-year-old ranked in the 130s is not a Masters 1000 title. Everyone involved knows this, including him.

What is genuinely at stake is smaller and, in a way, larger. He is trying to get his ranking back into a range where he does not need anyone's permission to enter tournaments. He is trying to string together enough matches that the body stops feeling like a hostile witness. He is trying, at an age when most of his contemporaries have moved into the commentary box, to still be a tennis player.

The backhand argument

Let us also be honest about the shallow reason to watch him, which is that he is one of the most pleasing players of his generation to look at.

The one-handed backhand is a nearly extinct shot. It is technically inferior for returning modern serves and defending high balls, which is why the coaching world quietly abandoned it, and the sport is measurably poorer for having done so. Dimitrov's is a beauty: high finish, full extension, the ball leaving the strings with topspin that makes it dip late. When he is moving well he plays a kind of tennis that feels handmade in an era of machined efficiency.

You get maybe two or three players per generation whose matches are worth watching regardless of the scoreline. He has been one of them for fifteen years, through the disappointing seasons and the glorious autumn and all the injuries since. The stylists get remembered longer than their results deserve, which is the game's small compensation for making them lose so often.

What a wild card is actually for

Tournaments hand out wild cards for three reasons: to help a young player, to sell tickets, and occasionally to do something decent for someone who has earned it. This year Cincinnati gave four of them to men who have won the biggest titles the sport offers, one of whom is playing his final season and one of whom won this exact tournament.

The tickets will sell. But there is a straightforward pleasure in a tournament remembering who won it, and in a crowd getting the chance to make a noise for a player at the end of his career rather than the beginning of it. Somebody in that stadium was there in 2017. Quite a few somebodies, probably.

He may lose in the first round. That is a completely plausible outcome and it would not diminish anything, because the interesting part already happened — in a gym in Bulgaria, in an empty practice court somewhere, in the moment a frightened man made himself swing through a forehand and find out whether his chest would hold.

If you are watching this week, find his match on the schedule and give it an hour. Not because you will see the tennis of 2017, but because you will see a person who has been given every rational reason to stop, and who keeps turning up anyway with the prettiest backhand in the building. That is worth an hour of anybody's evening.

Photo: Grigor Dimitrov at the 2023 DC Open by Hameltion, CC BY-SA 4.0, via Wikimedia Commons.