Riccardo Montolivo was born on 18 January 1985 in Milan. He came through Atalanta’s youth ranks before making his Serie A debut with La Dea during the 2004/05 season. His excellent form that campaign earned him a transfer to Fiorentina, where he played over 200 games across seven seasons and became the club’s captain. In 2012, he signed for Milan and went on to wear the captain’s armband a year later. He remained at the Rossoneri until 13 November 2019, the date when he announced his retirement from football.

Montolivo’s Italy adventure began on 17 October 2007 in Sofia, Bulgaria as the Azzurri ran out 2-0 winners against South Africa. He then took part in the Beijing Olympics before returning to the Italy fold after being called up by Marcello Lippi in October 2008. The midfielder was an ever-present in Lippi’s squad during the former Head Coach’s second spell in charge of the National Team and was involved in the 2009 Confederations Cup and the 2010 World Cup. Things remained the same with Prandelli in the dugout. Montolivo was one of the key players during EURO 2012 qualifying and then at the tournament itself, where he started in Italy’s defeat to Spain in the final. He took part in the 2013 Confederations Cup and was included in the squad for the 2014 World Cup, only to then get injured in a pre-tournament friendly against Ireland and miss out. In the Autumn of 2015, he wore the Azzurri shirt once more, earning three further caps in Italy’s EURO 2016 qualifying matches against Azerbaijan and Norway and a friendly fixture against Romania. In total, he made 66 appearances for the Azzurri, scoring twice in the process.