In 2009, while riding for , Tiralongo registered his best final result on a
Grand Tour, finishing the
Vuelta a España in eighth position after riding consistently in the mountain stages. He conceded a little over 9 minutes to the victor, Spaniard
Alejandro Valverde of . He joined Astana for the 2010 season, on a 2-year contract. In 2011, Tiralongo took a notable victory on
stage 19 of the
Giro d'Italia, a summit finish to
Macugnaga. He attacked in the final kilometers and went clear of the lead group, but was joined by
Alberto Contador () in the final few meters. He came first on the line, taking his first victory in more than ten years. In 2012, he won another stage in the
Giro d'Italia,
stage 7, which was a hilltop finish atop
Rocca di Cambio. With 500 meters to go, Tiralongo followed an attack initiated by
Michele Scarponi of and he passed Scarponi inside of the final 100 meters. He lay on the ground afterward, out of breath. On 24 April 2015, Tiralongo collected his first victory of the season in the final stage of the
Giro del Trentino. He passed the last climb (Passo Predaia) with a small leading group and won the sprint after the descent. On 17 May, he won Stage 9 of the
2015 Giro d'Italia. ==Major results==