2022: Maiden Challenger title, ATP debut In July, Maestrelli won his maiden
Challenger title at the
2022 Internazionali di Tennis Città di Verona. In October, Maestrelli received a wild card for his
ATP Tour debut at the
2022 Firenze Open, losing to eventual runner up
J. J. Wolf in the first round.
2023-2024: Top 150 In June, Maestrelli reached the top 150 following his
2023 Emilia-Romagna Open Challenger final showing in
Montechiarugolo, Parma, Italy.
2025: Three Challenger titles, back to top 150 In June, Maestrelli won his third
Challenger title at the
2025 Ion Țiriac Challenger, defeating
Luka Pavlovic in the final. As a result he returned to the top 200 in the singles rankings. ==Grand Slam performance timeline==