Di Carlo started his career in his native city, playing as a midfielder for the local Serie C2 team Real Cassino.

In his time there, he struggled to keep the crociati out of the relegation zone, only to be ultimately sacked on 10 March 2008 following a 1–2 home loss to Sampdoria.

[4] He guided Chievo to two consecutive mid-table placements in the Serie A, which were hailed as impressive results considering the difficulty of competing against more renowned teams with one of the lowest budgets in the league.

[6] Sampdoria's form in Serie A so far had been middling, with the Blucerchiati keeping a tight defence, but struggling to score, especially after the departures of Antonio Cassano and Giampaolo Pazzini.

[9] He then briefly served as head coach of Livorno at the end of the 2013–14 season in a desperate but ultimately unsuccessful attempt from the club to escape relegation.

[14] On 1 June 2022, Pordenone announced the hiring of Di Carlo as their new head coach, effective from 1 July, on a two-year deal.

[17] On 11 July 2023, Di Carlo was announced as the new head coach of Serie C club SPAL, signing a contract until the end of the season.

[21] He was sacked on 25 January 2025 after a 1–2 loss to Lucchese; the announcement was made by the club chairman, Massimo Pulcinelli, through an Instagram story just minutes after the end of the game.