In 2020, following the withdrawal of Alexandre Cougnaud and a positive test at the end of the 2020 Castellet 240 with Graff Racing, Milesi had the opportunity to join this same team in order to participate in the 24 Hours of Le Mans in the hands of an Oreca 07 in the LMP2 category with Vincent Capillaire and James Allen as co-drivers. Unfortunately, in their first participation, Milesi could not see the checkered flag after going off the track in the last hour of the race when Allen was at the wheel. With this first experience in the hands of an LMP2 and following the withdrawal of the Mexican driver Memo Rojas, Milesi had the opportunity to join the American team DragonSpeed in order to participate in the 4 Hours of Monza. This race went in the best possible way because the car finished in 3rd position. Unfortunately, a problem with the height of the non-compliant diffuser, the car was disqualified at the end of the race. Milesi then finished his year by taking part in the final of the Michelin Le Mans Cup with the CD Sport team in the hands of a Ligier JS P320.