position in Milan's youth system, winning the Torneo di Viareggio with the AC Milan Primavera side in 1999 and 2001. In 2001, following the sacking of manager Alberto Zaccheroni, he served as a caretaker manager for the senior club and coached Milan for the remainder of the 2000–01 Serie A season, alongside Cesare Maldini, helping the club to qualify for the UEFA Cup, before being replaced by Fatih Terim at the end of the season. In the 2001–02 season, Tassotti joined Milan's coaching staff under former teammate Carlo Ancelotti as an assistant manager, and retained his post after the latter's departure, under Leonardo, Massimiliano Allegri, Clarence Seedorf and Filippo Inzaghi. In January 2014, he acted as caretaker manager for one match, a 3–1 home win over Spezia for the campaign's Coppa Italia following Massimiliano Allegri's dismissal and before Clarence Seedorf's appointment. In July 2015, he began working as a talent scout for Milan. Ukraine national team Tassotti terminated his contract with Milan on 12 July 2016, concluding his 36-year career with the club. his contract was due to expire in June 2017. It was later reported Tassotti had taken an assistant coaching position with the Ukraine national team, along with Milan Youth System coach Andrea Maldera, under the national team's former assistant manager Andriy Shevchenko, who formerly also played for Milan as a striker and who was named the team's new head coach. Style of play Tassotti was mostly used as a right-back, but he could also play as central defender when necessary, and often played in this role earlier on in his career. He even played as a central or defensive midfielder on occasion. Regarded as one of Italy's greatest defenders, and as one of the best full-backs of his generation, he is mostly remembered for his role alongside Maldini, Baresi, Galli and Costacurta in the legendary Milan backline of the late 1980s and early 1990s, under Sacchi and Capello, which is considered one of the greatest defences of all-time. Tassotti was a tenacious defensive minded full-back who was known for his strength, anticipation and defensive awareness, as well as his marking ability, positional sense and tactical intelligence. These attributes made him extremely adept at reading the game and at covering defensively for his teammates, and allowed him to excel in Milan's zonal marking system, which used a high defensive line and the offside trap. While at Lazio, he