As a player, Cioffi was a defender. He started his career with Tuscan amateurs Sestese, which was followed by several other experience in the minor Italian leagues of Serie C1 and Serie C2. In January 2005 he joined Mantova, with whom he became a fan favourite, won a Serie C1 title and made his Serie B debut during the 2005–06 season. After an impressive Serie B campaign with Mantova, he was subsequently signed by Torino, with whom he made his Serie A debut during the 2006–07 season. He left Torino after one season to join Ascoli, which he left in 2010 for AlbinoLeffe as a free agent. He retired in 2012 after two seasons with Carpiwhere he won the league as captain getting the promotion from Lega Pro 2 to Lega Pro 1. In his last season with the club he lost the final to Be promoted in Serie B.
Managerial career
After his retirement, he stayed in Carpi as an assistant coach for the 2012–13 season. In July 2013 he was announced as new head coach of Lega Pro Seconda Divisione club Gavorrano; he was fired later in November due to poor results.Following his departure the squad had an horrible run of results, the club called him back but he refused because with some few games to go the relegation was just a formality. He subsequently relocated to Australia and worked for two years as youth coaches former for Eastern United FC, before moving back to Italy in November 2015 to accept an offer as youth coach for the Berretti team of third division club Südtirol.After just a month he signed as assistant manager with Al Jazira Club, almost in the relegation zone. He took charge of the team for two games winning the first with a net result 4-1 versus Emirates. Then the club appointed Henk Ten Cate as manager. Thanks his work the squad reached the ACL qualification for the following season, won the President Cup and after eleven years, the same season, went to the first round of the ACL winning the knock out game on an heart breacking penalty shot sequence. He left the club in February 2016 to accept an offer as Henk Ten Cate's assistant coach at Al Jazira Club. In December 2016 he joined the coaching staff of Gianfranco Zola at English Championship club Birmingham City.After the resignation of the manager all the staff left the club. In December 2017 he signed as assistant manager for Al DhafraFootball club who was challenging the relegation. The team, thanks to his work, was able to get a stable position in the table, several young players made their debut that season. Following Zola's resignations on 17 April 2017, his entire backroom staff, including Cioffi, left Birmingham too. In September 2018 he was named as new head coach of EFL League Two club Crawley Town who was fighting the relegation area, succeeding Harry Kewell. The first season he was able to guarantee the club’s status and to plan for the following season. He was the first manager to win in his home debut and for the first time in the history of the club to beat a Preamir league side making an amazing run in the Carabao Cup. He was able to bring the team to the 2nd round of the FA Cup and bringing the team close to the play off in a stable position. He was able to gamble, work on and improbe young players like Beryl Lubala and Panuthe Camara who became possibile future sell for the club. Following a poor run of result in the month of november, due to traumatic injuries of four starting eleven players, on 2 December 2019, Cioffi left Crawley by mutual consent. He was succeeded by John Yems.
