Raggi started his footballing career with Empoli, where he spent a total of four seasons with the first team.

[4] He was out-favoured by Giampiero Ventura in mid-season, who originally expected Raggi to play as a centre-back.

After the closure of the winter transfer window, Parisi and Masiello re-took the full-backs position, after the signing of centre-back Kamil Glik.

On 19 April 2017, after defeating Borussia Dortmund 6–3 on aggregate,[8] AS Monaco reached the semi–finals of the 2016–17 UEFA Champions League.

In September 2017, he signed a two-year contract extension on a €2 million annual salary, which would keep him at the club until June 2019,[10] with AS Monaco confirming Raggi's departure on 28 June 2019[11] On 24 March 2007, Raggi made his International debut for the Italy U-21 side against the England U21 team in a 3–3 draw at the new Wembley Stadium.