With an in-form Ronaldo on his side, Simoni won the UEFA Cup over Lazio in 1998, and managed a second-place finish in Serie A, behind Juventus.

[1] After a few other experiences, including Piacenza, Torino, and a brief disappointing spell in Bulgaria with CSKA Sofia,[1] Gigi Simoni led Ancona Calcio to Serie A in 2003, but was surprisingly fired before the start of the new season.

In February 2009, at the age of 70, Simoni accepted a job at Lega Pro Seconda Divisione's Gubbio, where he would serve as technical director until the end of the season.

Pecchia's term as Gubbio boss turned out however unsuccessful, and on 18 October 2011 Simoni agreed to serve as caretaker head coach for a Serie B game against his former club, league toppers Torino.

[4] The game ended in a surprising 1–0 win for his side, and led the club to keep Simoni in charge as long as a valid replacement coach would be found.