Grigor Dimitrov was on a crash course to face Novak Djokovic in the third round of the Monte Carlo Masters. That blockbuster matchup, however, never happened. And you won’t hear any complaints from Dimitrov. The Bulgarian has a rough 1-13 head-to-head record against Djokovic. But Alejandro Tabilo? He’s got something rare on his resume—a winning record against the 24-time Grand Slam champ. Tabilo stunned Djokovic in straight sets, 6-3, 6-4, to reach the round of 16 in the Principality. Now, it’s Dimitrov vs Tabilo for a place in the quarterfinals. Who will prevail?

Grigor Dimitrov vs Alejandro Tabilo: Preview

Grigor Dimitrov comes into this one as the fifteenth seed, but 2025 hasn’t exactly been kind to him. Injuries have slowed him down all season. The Bulgarian has retired from three matches already this year, including in the semifinal of the Brisbane International. He was defending his title there, but had to pull the plug mid-match against Jiri Lehecka. Even so, the Bulgarian showed some fire recently.

At the Miami Open, he reached the semifinals. That run ended with a 2-6, 3-6 loss to Novak Djokovic. Still, it was a sign that the former World No. 3 was finding his groove again. He’s brought some of that rhythm to Monte Carlo.

In the first round, he beat Nicolas Jarry 6-3, 6-4. Then, in round two, he had to dig deep. He dropped the first set to local wildcard Valentin Vacherot but came back strong: 4-6, 6-3, 6-1.

Now over to Alejandro Tabilo. What was his 2025 record before this tournament? Two wins out of eleven matches. The start of the year was brutal, with six straight losses. The Chilean managed one win at Indian Wells and one in Miami, but didn’t stick around long in either event. In both, he exited the very next round. But something has clicked in Monte Carlo.

Tabilo opened his campaign with a comeback win over 2014 champion Stan Wawrinka. It wasn’t pretty, but it was gritty: 1-6, 7-5, 7-5. Then came the shocker. In round two, he took out third seed and two-time champion Novak Djokovic in straight sets.

Grigor Dimitrov vs Alejandro Tabilo: Head-to-Head

Dimitrov and Tabilo have actually met twice before, and on both occasions, it was Dimitrov who came out victorious.

• 2024 Laver Cup Round Robin: Dimitrov won 7-6(4) 7-6(2)
• 2024 ATP Masters 1000 Miami Open Round of 64: Dimitrov won 6-7(5) 7-6(5) 6-2

Prediction: Dimitrov to win in three sets

Yes, Tabilo stunned Djokovic, but it wasn’t all his doing. The Serbian legend gave away plenty of points, and those kinds of gifts won’t be on offer against Dimitrov.

While Tabilo has a solid 61% career win rate on clay, Dimitrov is no slouch on the surface. He’s been to the semifinals here twice. He also just came back from a set down to beat Vacherot. That shows he knows how to find answers when things aren’t going his way.

Still, don’t count out the Chilean’s lefty forehand. That crosscourt shot could cause problems for Dimitrov’s one-handed backhand. But Dimitrov is no stranger to long rallies, and his defense might hold up just fine.

The Bulgarian’s second-serve return game has looked sharp, too. He won 74% of those points against Vacherot. That could be a key area, especially since Tabilo’s second serve isn’t the strongest part of his game.

On paper, this feels close. Tabilo’s win over Djokovic proves he’s dangerous when in form. But Dimitrov’s experience and better track record on clay give him the edge. It might go three sets, and it won’t be easy, but the numbers and history favor the Bulgarian.