Diallo Upsets Dimitrov to Reach First Masters 1000 Quarter-Final in Madrid

By Pete Borkowski

April 30, 2025

Gabriel Diallo 2025 Madrid Open Martin Sidorjak 5

Gabriel Diallo is not getting lucky any more in Madrid, he is getting the job done all on his own. 

The 23-year-old from Montreal’s dream run at the Mutua Madrid Open hit new heights on Wednesday as he scored the biggest win of his career to-date, defeating Grigor Dimitrov in three sets to reach his first Masters 1000 quarter-final. At 16 in the world, Dimitrov is the highest-ranked player Diallo has beaten. 

Dimitrov seemed well on his way to victory when he took the first set and had three match points in the second but the Canadian, who only got into the main draw as a lucky loser, refused to back down, playing gusty tennis to force a decider which he ultimately won, punching his ticket to the last eight with a 5-7, 7-6(7), 6-4 victory.  

This match was all about which points were won, not how many. Dimitrov actually won one more point than Diallo, had more winners (39 to 31), more aces (14 to 8), and won more of his first serve points, but the Canadian won the points that mattered most, especially in the second-set tiebreak.  

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He also defended his serve better, putting an impressive 77 per cent of first serves in play, winning 77 per cent of those points, and limited Dimitrov to just a single break point in the match.  

Through the first 10 games, both men faced little opposition on their own serve. They each had to rally from love-30 down once but the returner never managed more than two points in a game until 5-5. 

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In the 11th game, some spectacular shot-making from Dimitrov created a breakthrough. He pushed Diallo to deuce for the first time in the match and then whipped up a tight passing shot that the Canadian could not handle to create the first break point. There, the Bulgarian punched an impressive lunging volley over for a winner to secure the decisive break. 

Diallo had a chance to gain the upper hand early in the second set when Dimitrov double-faulted to go down 15-40 in the fourth game. The Canadian missed his return on the first break point and Dimitrov found a forehand winner on the second to erase the threat. 

That was the only challenge either man faced on serve in the set. Dimitrov did not lose another point on serve after that double fault until the tiebreak, while the Canadian never trailed in his own service games. 

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It seemed like Dimitrov was going to get out in two sets when he led the tiebreaker 6-4, but Diallo was not going away quietly. The Bulgarian missed a forehand on the first match point on his own serve and then the Canadian lazered a forehand winner to save the second. Dimitrov had another chance on his own serve at 7-6 but sent another forehand long. When Diallo had a chance to close out the set at 8-7, he blasted an ace to extend the match.  

In the opening game of the third set, Dimitrov again double faulted to go down 15-40 and this time, he sent a forehand long on the second break point to give Diallo an immediate lead and even more momentum. 

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Once he had the break, the Montrealer locked in. At times in the third set, he almost resembled his fellow Canadian giant Milos Raonic, seemingly able to deliver unreturnable serves at will. He backed up the break with a hold to love and never gave Dimitrov a sniff at drawing even, trailing just once on his own serve in the decider (love-15 in the fourth game). Having saved the three match points in the second, he finished off the win on his first with another big serve. 

Diallo will play the winner between world No. 7 Alex de Minaur, who beat Denis Shapovalov in the third round, and No. 11 Lorenzo Musetti in the quarter-finals.  

Feature Photo : Martin Sidorjak