Di Cesare career began with
Lazio's youth system. During the summer of 2001, he accepted an offer from
Chelsea, initially joining the
Blues' reserve team. However, he failed to break into the first team, and left England in January 2004 without making a single appearance, joining
Avellino in a temporary deal. Di Cesare suffered a serious knee injury. and
Como for a trial. Di Cesare then went on to play in Serie B with
AlbinoLeffe,
Catanzaro and
Mantova, joining the
Virgiliani in January 2006.
Mantova Di Cesare only played twice for the Veneto side in
2005–06 Serie B. In the next two seasons, he played 46 times out of a possible 84 Serie B games.
Vicenza In June 2008, Di Cesare moved to
Vicenza along with
Simone Calori for €1 million and €500,000 respectively. Di Cesare only briefly played again in the first season with his new club (13 times in Serie B); Di Cesare played 33 games in
2009–10 Serie B.
Torino In the final year of his contract, Vicenza decided to sell him to
Torino for €250,000 in a three-year contract (€750,000 short with the original price or €83,333 with the residual value of the contract), while Calori (who never played for the club) was released for free with a write-down of €166,667. Di Cesare made 50 out of possible 84 Serie B appearances with the
Toro, winning the promotion back to Serie A. Di Cesare played nine times in
2012–13 Serie A. In June 2013, Di Cesare also obtained a license as youth team coach.
Brescia On 8 August 2013, Di Cesare joined Serie B team
Brescia. In
2015–16 Serie B, he did not receive a shirt number on 5 August. A week later he was sold to
Bari.
Bari Di Cesare signed a two-year contract with Bari on 12 August 2015.
Parma On 31 January 2017, Di Cesare was signed by
Parma in a -year contract.
Return to Bari In September 2018, after being released by Parma, Di Cesare agreed to re-join Bari, following the club's refoundation in the
Serie D league. He captained Bari to two promotions, leading the club back to Serie B and narrowly missing promotion to Serie A after losing to
Cagliari in the
2022–23 Serie B playoff finals. He retired in June 2024 at the age of 41, after being instrumental in Bari's escape from relegation in a playoff match against
Ternana, scoring the first goal in a 3–0 away win against the
rossoverdi. ==Honours==