[3] Successively, Filippi followed Boscaglia on all of his later coaching jobs at Novara, Brescia for a second time, Virtus Entella and, in 2020, Palermo.
On 27 February 2021, Filippi was promoted to head coach of Palermo after the Rosanero board decided to sack Boscaglia from his role.
[4] Under his tenure in the second half of the 2020–21 Serie C season, results significantly improved and Palermo manage to qualify to the promotion playoffs, from where they were eliminated in the third round by third-placed Avellino.
These positive results led Palermo to confirm that Filippi was also in charge of the first team for the following 2021–22 Serie C season.
[5] He was dismissed from his position on 24 December 2021, following a 0–2 loss against Latina that left Palermo in fifth place, eleven points behind league leaders Bari.