After three years with Bardiani–CSF, Ciccone joined Trek–Segafredo on an initial two-year contract from the 2019 season. At the Giro d'Italia, Ciccone led the mountains classification for all but one stage, winning the jersey with more than twice as many points than the runner-up Fausto Masnada. He finished 16th overall, with a victory on stage sixteen, a finish at Ponte di Legno. After this, Ciccone was named in the startlist for the Tour de France. During the sixth stage to La Planche des Belles Filles, he was part of a breakaway which survived to the finish line. Ciccone managed to take over the race leader's yellow jersey from Julian Alaphilippe despite fading in the final metres of the climb. He held the lead for two days, before Alaphilippe retook the jersey after gaining twenty seconds on the run-in to the finish in Saint-Étienne. Ciccone also held the lead of the young rider classification for four days, ultimately finishing just outside the top thirty placings overall and sixth in the young rider standings.