Grigor Dimitrov continues to struggle even after dropping down to the ATP Challenger Tour.
Dimitrov suffered a pectoral muscle injury at Wimbledon last year, and was forced to retire after leading eventual champion Jannik Sinner by two sets to love.
The former world number three has only won three matches since then, with Dimitrov falling to his lowest ranking in a decade as a result.
Dimitrov will have to play French Open qualifying next month, and he has dropped down to the Challenger Tour to try to rediscover his form, but it has not quite gone to plan.
Grigor Dimitrov loses to the world number 312 at Challenger tournament
Dimitrov had not played on the Challenger Tour since 2012, but after losing in the first round of the Madrid Open he took a wildcard for the lower-level event in Aix-en-Provence.
Looking to win just his third match of the 2026 season, Dimitrov would take on qualifier and world number 312 Pol Martin Tiffon.
Despite being the much more established player, Dimitrov was beaten by Tiffon 6-3, 6-4 in his fifth consecutive defeat.
Tiffon is the lowest-ranked player to beat Dimitrov since 2019, when the Bulgarian was beaten by world number 405 Kevin King in Atlanta.
The only two players Dimitrov has beaten this year are Pablo Carreno Busta (Brisbane) and Terence Atmane (Indian Wells).
| Tournaments Grigor Dimitrov has played in 2026 | Result |
| Brisbane International | Lost in the second round to Raphael Collignon |
| Australian Open | Lost in the first round to Tomas Machac |
| Dallas Open | Lost in the first round to Alex Michelsen |
| Mexican Open | Lost in the first round to Terence Atmane |
| Indian Wells | Lost in the second round to Carlos Alcaraz |
| Miami Open | Lost in the first round to Raphael Collignon |
| Monte Carlo Masters | Lost in the first round to Tomas Martin Etcheverry |
| Madrid Open | Lost in the first round to Adolfo Daniel Vallejo |
| Aix-en-Provence Challenger | Lost in the first round to Pol Martin Tiffon |
Grigor Dimitrov now set to fall to his lowest ranking since 2010
Dimitrov had already fallen outside the top 100 and will have to play Grand Slam qualifying for the first time since 2012 at the French Open.
This is only going to get worse for Dimitrov, who will suffer another drop down the rankings after his latest defeats.
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Dimitrov reached the last-16 at the Madrid Open last year and is now the world number 168 in the live ATP rankings.
This will be Dimitrov’s lowest ranking since September 2010, and will now make it even more difficult for him to enter ATP tournaments without requiring wildcards.
Dimitrov will now head to Rome for the Italian Open, where he is a former semifinalist, but will be in the qualifying draw this year.
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