After serving as a head scout for his former team Milan from February 1999, Maldini briefly returned to coach the Milan first team in March 2001, serving as an interim manager for the club (whose captain was his son, Paolo) alongside youth coach Mauro Tassotti, following Alberto Zaccheroni's sacking, and led the squad for their final games of the season. Although the club endured a disappointing season, finishing in sixth place and failing to qualify for the Champions League, Maldini did lead the team to a memorable 6–0 victory over cross-city rivals Inter in the Milan Derby on 11 May; the result was Inter's worst-ever home defeat in Serie A, and Milan's biggest league win in the Derby. After helping the club to qualify for the UEFA Cup, Maldini was replaced by Fatih Terim the following season, although he initially remained with the club as an advisor to the coach.
