Daniil Medvedev and Alexander Zverev are the current number one and two but neither of them has won a trophy this season yet.
In a fascinating twist of circumstances both the current world number one Medvedev and the current number, two Zverev have not won trophies this year. Medvedev played his first final of the year in Melbourne where he witnessed the superb comeback of Nadal to win the Australian Open. The Russian played his next final in Den Bosch losing to Van Rijthoven.
He also played in the Halle final but lost to Hubert Hurkacz. Zverev too played finals with his first one of the year coming in Montpellier. Alexander Bublik proved better there. His second one came at the Madrid Masters but Alcaraz proved better in that one. They are not the only players that have not won a trophy this year.
Three more players that are ranked inside the top 20 have not won a trophy yet. Diego Schwartzman at number 15 played two finals. One was in Bueno Aires but Ruud proved better and the other in Rio de Janeiro with Alcaraz proving better. Cilic at 16 also did not win a trophy this year but he also did not play in a final. The last player is Dimitrov at 19 and he too did not play in a single final this year.