Matteo Berrettini scored his first win over Novak Djokovic in five tries. What does it mean?

No matter how well an opponent may be playing against Novak Djokovic, or how far he may seem to be ahead, a moment of truth will arrive. Djokovic, with his uncanny ability to produce his best tennis just when it looks like he’s lost all hope, will find a way to make him nervous. He’ll keep the door open a few inches and force the other guy to slam it shut. Recent tennis history is littered with those who couldn’t.

On Tuesday in Doha, Matteo Berrettini faced that moment of truth. The 28-year-old Italian had lost all four of his previous matches to Djokovic. The last three had come at Grand Slams, and all three had gone to four sets. But each time it was the older man who had worn down the younger.

Now, four years since their last meeting, Berrettini was up a set and a break in Doha, and was in full bully mode in the rallies. But could he close?

Berrettini wasn’t just trying for his first win over Djokovic. He was also looking for his first significant victory of 2025. After two seasons spent mostly on the sidelines due to injury, he found his way back into the conversation in 2024, and ended the year on a high, by teaming with Jannik Sinner to win the Davis Cup for Italy. In the past, Davis Cup success has propelled other players to career seasons—including Djokovic, in his memorable 2011 campaign—and Berrettini looked poised to ride that momentum higher. But instead of leaping out of the gate in 2025, he stumbled. He was 1-3 on the season coming into today.

From the start on Tuesday, Berrettini stood up on the baseline and traded punches with Djokovic. The points were spirited and fast-paced, with both guys jockeying for an immediate advantage. It looked like Djokovic had found it when he earned two break points at 3-2, but Berrettini, who finished with 13 aces, wiped them away with a series of hammer-blow serves.

By the tiebreaker, he had taken control. Berrettini won the first three points, and closed the set with a pair of forehand-backhand combinations that Djokovic couldn’t handle. The trend continued in the opening games of the second set, when Berrettini broke with an inside-out forehand, and held at love.

He’s always ready to come back. I had to stay focused to keep playing the way I was playing, aggressive. Matteo Berrettini

But Djokovic, as he tends to do, hung around. He relaxed and held serve twice. With Berrettini serving at 4-2, he went up 0-30. Djokovic was grunting and into it again, while the Italian looked nervous as he sliced a backhand into the net. This was the moment of truth.

Berrettini handled it by doing the same thing he had done to gain his lead: By taking the racquet out of Djokovic’s hand. He started with a serve-forehand combination. He followed with a service winner. He followed that with an ace. And he held by winning a long rally, the type of rally where Djokovic usually has the upper hand. Five minutes later, the match was over, 7-6 (4), 6-2.

“It’s something I’ve been looking to do for a really long time,” said Berrettini, who made 75 percent of his first serves and won 80 percent of those points. “To be back at this level, all the hard work I’ve been putting in, it really worked well.”

“He’s always ready to come back. I had to stay focused to keep playing the way I was playing, aggressive.”

Berrettini faced his moment of truth and passed the test. It’s just a first-round win, but first-round wins don’t get much more satisfying.