The first real test for the player from Sesto?

So far, world number one Jannik Sinner has lived up to expectations at the All England Lawn Tennis and Croquet Club. The Sextner marched into the round of 16 at breakneck speed. He has yet to drop a single service game, let alone a set, on his way to the last 16. Accordingly, the tip for Jannik Sinner against Grigor Dimitrov is that he will also make short work of the Bulgarian.

However, it should be noted that Grigor Dimitrov – unofficial world champion in 2017, after all – is well suited to grass with his playing style. Early in his career, he earned the nickname “Baby Federer” in reference to the Swiss player, who remains the record winner of the men’s singles title at Wimbledon. This makes it all the more interesting to predict that Jannik Sinner will now face his first real test against Grigor Dimitrov, who is ranked number one in the world.

Especially in sets where the South Tyrolean temporarily loses his serve – even against Pedro Martinez in the third round, he slipped below 50 percent on his first serve in the second set, which he won 6-3 – Grigor Dimitrov could well be there to take advantage. Against this backdrop, another Sinner victory in record time does not seem to be a foregone conclusion. Instead, we could even see the first set lost in the tournament, although an exit for the Italian would be a big surprise.

Jannik Sinner – Statistics & current form

The 23-year-old Italian Jannik Sinner is certainly in high demand as the world number one at Wimbledon 2025. So far, he has fully lived up to his role as favorite. With three wins, the Sextner has increased his record for the year to 22 wins from 25 singles matches and has reached the last 16 at Wimbledon for the fourth time in a row. He has mastered this round for the last three years, even though the only Grand Slam tournament played on grass is the only one of the four major ATP Tour tournaments where the South Tyrolean has yet to reach the final.

Nevertheless, the world number one recorded his 16th victory in his 20th Wimbledon singles match, reaching the second week of the tournament once again, where he now faces Grigor Dimitrov, against whom he has won four of their five singles matches. Accordingly, the tip for Jannik Sinner against Grigor Dimitrov is that he will win again this time.

Jannik Sinner could even afford to be slightly unfocused

Nevertheless, Jannik Sinner is now facing a seeded opponent for the first time in the tournament and could possibly be punished for any lapses in concentration. His recent 3-0 victory over Pedro Martinez in the third round was as clear as could be (6-1, 6-3, and 6-1). Nevertheless, it should be noted that in the second set, the South Tyrolean’s first serve only landed in 49 percent of all cases, allowing his Spanish opponent to repeatedly come back into the game.

However, Pedro Martinez failed to convert four break points, which meant that even at a critical moment when the Spaniard could have levelled the score at 4:4, the match did not become close again. Instead, the South Tyrolean regained his concentration, took the game to 5:3 and then played out the match with confidence. Nevertheless, his first serve only landed in 58 percent of all cases throughout the match, which should also give Grigor Dimitrov plenty of room for counterplay. However, it can be assumed that the “Baby Federer,” who is strong on grass, will use this space more effectively than the 23-year-old’s previous opponents did…

Grigor Dimitrov – Statistics & current form

The 34-year-old Bulgarian Grigor Dimitrov has been playing professionally on the ATP Tour since 2008. The player, once dubbed “Baby Federer,” was considered an absolute promise for the future early on. Dimi quickly rose to the top 20 in the ATP world rankings and secured his first singles titles before celebrating his definitive breakthrough in the 2017 season. His first major title at the 2017 Western & Southern Open was followed by qualification for the ATP Finals, which he won in style.

However, that unofficial world title then became a heavy burden for “G-Force,” as it took him almost seven years to win another singles title. Not because he was set back by injuries, but because the results were consistently lacking. Dimi has not missed a single Grand Slam tournament since 2010. At Wimbledon, the 34-year-old has reached the round of 16 in each of the last two years, where his journey then came to an end.

Grigor Dimitrov with a poor record against the top stars on the tour

Even now, everything points to the end for the world number 21. At Bet365, where new customers can get up to €100 in betting credits with the Bet365 bonus, the odds for Jannik Sinner against Grigor Dimitrov are 13.00 for a victory for the Bulgarian, who has won only one of five singles matches against the player from Sexten so far. In general, the former “Baby Federer” has been hampered by his poor record against top 10 players. Dimi has won only 43 of his 135 singles matches against top 10 players in his career. He also lost all three matches in 2025.

However, Dimi proved that he does not lack basic playing strength in the third round, when he swept Sebastian Ofner (ATP 165) off the court 3-0 (6-3, 6-4, and 7-6). The 34-year-old scored with his first serve in 81 percent of all cases against the Styrian and even achieved an impressive 60 percent with his second serve. Grigor Dimitrov allowed just three break points, two of which he saved. This could now also be a factor against Jannik Sinner.

Jannik Sinner – Grigor Dimitrov Head-to-head record / H2H record

Head to head: 4:1

The two athletes have faced each other five times so far, with Grigor Dimitrov only managing to beat Jannik Sinner in their very first encounter, which dates back to September 2020. The two players last faced each other in the quarterfinals of the 2024 French Open, when the Italian recorded a clean 3-0 victory over the Bulgarian.

Jannik Sinner – Grigor Dimitrov Tip

Once again, the betting odds from the best bookmakers are heavily in favor of Jannik Sinner against Grigor Dimitrov, with the South Tyrolean having lost only three of his 25 singles matches in the 2025 calendar year. The Italian has dominated his opponents at the Wimbledon Championships so far, but could now face some resistance from a very experienced former world champion. The risk of stumbling is not huge, but we believe that the Bulgarian, once known as “Baby Federer,” is capable of causing problems for the world number one.

Against this backdrop, the prediction that Jannik Sinner will lose a set to Grigor Dimitrov in the 2025 Wimbledon Championships is very promising. ODDSET offers odds of 2.35 for this outcome, which we are backing with three out of ten units.