Born in 2000, Montella began his competitive career at sixteen years old, entering the FIM CEV Moto3 Junior World Championship with the Sic58 Squadra Corse team in 2016, the same squad that partnered him alongside future MotoGP contender Tony Arbolino. Over three seasons with Sic58 he steadily improved his consistency, accumulating a career-best 34 points and seventeenth in the standings by 2018.
In 2018 Montella made two wild-card appearances in the Moto3 World Championship at the San Marino and Australian Grands Prix, finishing nineteenth and sixteenth respectively without points.
For 2019 he moved up to the FIM CEV Moto2 European Championship with Speed Up's Team Ciatti alongside Tommaso Marcon, recording two third-place finishes and ending the year seventh in the standings with 77 points.
The 2020 season proved transformative. Montella dominated the CEV Moto2 series, winning the opening six rounds and eight of eleven races in total, finishing in the top two on ten occasions. His sole retirement came at Aragon. He clinched the title by 44 points over Niki Tuuli, a performance commanding enough to earn him a full-time Moto2 World Championship seat with Speed Up for the following year.
Montella's transition to the full Moto2 World Championship in 2021 proved difficult. He failed to score points in his first four races of the season, then suffered a wrist injury during practice at the French Grand Prix that required surgery and ruled him out of five consecutive events. His replacement, Fermín Aldeguer, scored points on debut, intensifying scrutiny on Montella's performances. He returned for the Austrian double-header but again went pointless. The team temporarily stood him down for the Silverstone and Aragon rounds to allow further recovery, again replaced by Aldeguer, who claimed seventh place at Aragon. When Montella returned at the next round and crashed out without points, Speed Up terminated his contract.
Yamaha offered Montella a wild-card entry for the 2021 Supersport World Championship at Portimão. He seized the opportunity decisively, finishing tenth in race one and sixth in race two, signalling that he retained the outright pace that had impressed in the junior series.
In November 2021, Kawasaki's Puccetti team signed Montella for the 2022 WorldSSP season, replacing Philipp Öttl who moved to World Superbike. Montella established himself as a regular frontrunner over the course of 2022.
For 2023 he joined the Barni Spark Racing Team on a Ducati, demonstrating immediate speed in testing and qualifying. His season was disrupted at Phillip Island during Race 1, when a collision with Adrián Huertas—who had fallen directly in front of him on a wet circuit—resulted in a compound fracture of his right clavicle. The race was red-flagged following the serious accident.
In 2024 Montella delivered his most complete season, claiming seven victories and finishing third in the final WorldSSP standings.
His consistent performances across 2023 and 2024 earned Montella a step to the Superbike World Championship for 2025, remaining with the Barni Spark Racing Team and partnered by former MotoGP race winner Danilo Petrucci. The promotion represented the culmination of a career rebuilt in the Supersport class after the difficulties of his Moto2 campaign.
Montella's trajectory illustrates the value of feeder championships as a second avenue to top-level competition. His dominance in the 2020 CEV Moto2 series remains one of the most commanding single-season performances in European junior road racing. The 2021 Moto2 experience, though brief and unsuccessful, made his subsequent WorldSSP resurgence—culminating in seven wins in 2024—a story of resilience within the sport.