[3] Lippi retained the Coach of the Year award the following season, when Juventus secured the domestic title again,[4] yet lost the Champions League Final to "perennial German underdogs" Borussia Dortmund.
[8] The following season, a fifth-place finish from newly promoted Chievo, and subsequent qualification for the 2002–03 UEFA Cup, ensured the Coach of the Year was awarded to Luigi Delneri.
[11][12] The 2003–04 season saw Milan claim their first Serie A title in five years, finishing eleven points ahead of nearest rivals Roma.
[17] A fourth place league finish for ACF Fiorentina and an appearance in the semi-finals of the 2007–08 UEFA Cup saw Cesare Prandelli as recipient of the Coach of the Year award in 2008.
[18][10] Portuguese coach José Mourinho became the second non-Italian to win the award when he led Internazionale to the Serie A title in the 2008–09 season, along with victory in the 2008 Supercoppa Italiana.
[21] Having led the club to league success and the semi-finals of the Coppa Italia, he was awarded the Coach of the Year title, presented at the "Gran Galà del Calcio" which replaced the previous ceremony.
Former player Antonio Conte succeeded Delneri as Juventus manager and led the club to their first league title in nine years, along with a losing appearance in the final of the Coppa Italia.
[26][27] Allegri led Juventus to their fifth consecutive Serie A title in the 2015–16 season, also winning both the Supercoppa and the Coppa Italia, and retained the Coach of the Year trophy.