Montecalvo attended St. John Vianney High School in New Jersey. His early professional racing included stints in the KONI Sports Car Challenge GS class in 2009 and in the IMSA Prototype Lites L1 class in 2010, where he drove for Gunnar Racing and recorded a win to finish 11th in the championship. He also competed in the American Le Mans Series LMPC class in 2010 with Genoa Racing and in 2011 with CORE Autosport, finishing second in class in the 2011 ALMS LMPC standings.
From 2012 onward he transitioned primarily to GT machinery. In 2013 he raced in the European Le Mans Series LMGTE class with Ram Racing, campaigning a Ferrari 458 Italia GT2, and finished fifth in class in the ELMS standings.
Montecalvo made his 24 Hours of Le Mans debut in 2012 driving for Luxury Racing in the GTE Am class alongside Pierre Ehret and Gunnar Jeannette in a Ferrari 458 Italia GTC. The team qualified fourth in class but retired after 146 laps due to crash damage. He returned to Le Mans in 2014 as a late replacement for Enzo Potolicchio in the 8 Star Motorsports GTE Am entry, co-driving with Gianluca Roda and Paolo Ruberti in a Ferrari 458 Italia GT2. The car completed 330 laps to finish fourth in class.
In 2015, racing for DragonSpeed, Montecalvo secured the GTA class championship in the Pirelli World Challenge. Over the 20-race season he took seven victories, six pole positions, six fastest laps, and fourteen podium finishes, accumulating 2,073 points to claim the class title. He returned to the series in 2016 with DIME Racing, winning two further races, recording five pole positions, and finishing third in the GTA standings. In 2017 he competed in the SprintX GT Pro-Am category for AIM Autosport, taking five pole positions, and also made two GTS class appearances with ANSA Motorsports.
Montecalvo made his first IMSA appearances in 2014 with PR1/Mathiasen Motorsports in the Prototype Challenge class, finishing fourth in the championship. He also contested the Daytona 24 Hours and Le Mans that year. Partial GTD seasons followed in 2017 with Alex Job Racing in an Audi R8 LMS and in 2018 with Scuderia Corsa in a Ferrari 488 GT3.
From 2019 he became a permanent fixture in the GTD class with AIM Vasser Sullivan, initially alongside Townsend Bell in the Lexus RC F GT3. The partnership delivered consistent results, with Montecalvo finishing eighth in the GTD standings in both 2021 and 2022. In August 2020, at Road America, Montecalvo claimed his first IMSA class victory.
In 2023, paired with Aaron Telitz in their second consecutive season together, Montecalvo scored his second IMSA win at the Sahlen's Six Hours of The Glen at Watkins Glen International. The victory was part of a Lexus sweep of the GT classes at that event. He finished third in the GTD championship standings at the close of the 2023 season — his best IMSA seasonal result. In 2024 he recorded three pole positions and finished seventh in GTD standings. He has continued with Vasser Sullivan Racing into 2025 and 2026.
Across his IMSA career Montecalvo has accumulated 1 win (in GTD class, at Road America in 2020 with AIM Vasser Sullivan), 4 pole positions in GTD, and 11 podiums. His Pirelli World Challenge record includes 9 victories, 11 pole positions, and 14 podiums across GTA and GTS competition.
Montecalvo has described himself as not a full-time professional racing driver, combining his motorsport career with his role at his family's recycling business. This semi-professional approach has characterised his career throughout, making his consistent front-running results in both national GT and international endurance competition a notable achievement.
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