He found his opportunities limited in his final season, with manager Sven-Göran Eriksson preferring Alen Bokšić and Roberto Mancini in attack and sought a move away.

His time in west London proved luckless, and ultimately only scored one competitive goal for the club in ten appearances, which came against Liverpool in a 1–1 draw at Anfield.

[3][4] His Chelsea career was cut short by a cruciate ligament injury sustained during a collision with West Ham goalkeeper Shaka Hislop in November 1998.

[8] He was a member of the Italy squad that reached the final of USA 94 under manager Arrigo Sacchi, losing out to Brazil on penalties following a goalless draw.

[15][16] Despite sealing Italy's qualification for the 1998 World Cup with the only goal in the second leg play-off against Russia to advance 2–1 on aggregate on 15 November 1997,[17] he failed to make the squad for the final tournament under Cesare Maldini.

On 24 July 2006, he was appointed head coach of the Italy U-21 national team alongside former Chelsea teammate Gianfranco Zola as his assistant, succeeding Claudio Gentile.

[24] In his coaching tenure, Casiraghi led the Azzurrini into the 2007 UEFA European Under-21 Championship, ending in fifth place after having eliminated Spain in the qualifying phase.

[27] In December 2016, he joined EFL Championship club Birmingham City as an assistant coach, again reuniting with Zola,[28] as he had previously served in a similar role at Cagliari[29] and Al-Arabi.