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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.

After retiring in 1997, Tassotti remained connected to Milan in several positions: he worked as a youth coach, as an assistant manager, as a caretaker manager and subsequently as a talent scout, until he left the club in 2016 to join the Ukrainian national side as an assistant coach.

Following his retirement in 1997, Tassotti took up a coaching position in Milan's youth system, winning the Torneo di Viareggio with the 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.

Under Capello, Tassotti would go on to reach three consecutive Champions League finals with Milan, winning the Champions League in 1994 as captain, due to the absence of Franco Baresi, and also reaching the final in 1993 and 1995. He also won three consecutive Serie A titles with the club in the 1991–92, 1992–93 and the 1993–94 seasons, adding another during the 1995–96 season, in addition to the 1994 UEFA Super Cup and three consecutive Supercoppa Italiana titles between 1992 and 1994. In the 1991–92 season, Milan won the title unbeaten, scoring a record 74 goals, and remained undefeated for a record 58 matches in Serie A. In 1993–94, Tassotti once again helped Milan finish the league with the best defence, only conceding 15 goals. In his last few seasons at Milan under Capello, he began to be used less frequently, due to his advancing age and the emergence of Christian Panucci in his position. Along with his teammate Baresi, Tassotti retired from the club at the conclusion of the 1996–97 season. In total, he made 429 Serie A appearances with Milan, scoring 8 goals, and 583 total club appearances, scoring 10 goals.

After featuring in Italy's 1994 World Cup qualifying matches and international friendlies under Sacchi, Tassotti played in the 1994 edition in the United States, where Italy went on to reach the final, losing to Brazil on penalties. This would be the only tournament in which he would participate with Italy. In the group stage, Tassotti started the 1–0 defeat to the Republic of Ireland and his next appearance was the quarter-final match against Spain. However, in the quarter-final match, Tassotti elbowed Spanish midfielder Luis Enrique in the face during stoppage time in the second half, breaking the Spaniard's nose. The gesture was not seen by the referee, and Tassotti was not called for a foul or cautioned at the time. Italy won the match 2–1. After reviewing the game, FIFA officials banned Tassotti for eight matches, the longest-such ban in World Cup history until Luis Suarez’s ban in 2014. Tassotti never played internationally again. Tassotti later stated he had instantly and deeply regretted his actions, describing them as "stupid", although he would also state the gesture had not been premeditated but purely instinctive, as Luis Enrique had been pulling his shirt. He later personally apologised to Luis Enrique. In total, Tassotti made 7 appearances for Italy between 1992 and 1994.

Tassotti did not win his first cap for Italy until age 32, under Arrigo Sacchi, in a 2–2 home draw against Switzerland in a 1994 FIFA World Cup qualifier on 14 October 1992. This was partly because of an abundance of other world class Italian defenders, as he was constantly overlooked by Sacchi's predecessor Azeglio Vicini, who preferred to deploy full-backs he had worked with during his tenure as Italy's under-21 coach, despite Tassotti's excellent club performances. Tassotti had previously played for Italy at under-21 level, and he represented the nation at the 1988 Summer Olympics, alongside Paolo Maldini, where Italy reached the semi-finals, finishing in fourth place.

An Italian international in the early 1990s, Tassotti only came into the national side under Sacchi, when he was already in his 30s, helping Italy to qualify for the 1994 FIFA World Cup. Tassotti would go on to represent his nation at the final tournament, winning a runners-up medal, although he was banned for the latter half of the tournament. Prior to his Italy senior career, he had previously also represented Italy at under-21 level, and participated at the 1988 Olympics with the under-23 team, finishing in fourth place.

Following Lazio's and Milan's relegation to Serie B due to their involvement in the 1980 match-fixing scandal, he was called upon by the Milanese squad and transferred to the side, becoming a first-team member alongside captain and defender Franco Baresi, as well as Filippo Galli, during a dark period in Milan's footballing history, under manager Nils Liedholm. He made his Milan debut on 24 August 1980, in Serie B, in a 1–0 home win over Catania. Milan won the Serie B title that season to return to Serie A, with Tassotti emerging as one of the club's best performers. Despite winning the Mitropa Cup the following season, Milan were unable to remain in Serie A, finishing third last, and were relegated once again to Serie B. Milan were able to win Serie B again the following season to return to Serie A. Although this was a fairly bleak period in the club's history, as they failed to dominate in the league or capture a trophy, the squad did reach the Coppa Italia final during the 1984–85 season, and were able to regularly qualify for the European competitions, frequently finishing in the top half of the table.

Tassotti became a central figure in the Milan squad of the late 1980s and early 1990s under Arrigo Sacchi, and subsequently Fabio Capello, usually wearing the number 2 shirt. Tassotti was a key component of a strong defence alongside Paolo Maldini, Franco Baresi and Alessandro Costacurta, playing predominantly as a right-back and on occasion as a centre-back, in front of goalkeepers Giovanni Galli, and subsequently Sebastiano Rossi. The back four of the Milan side of this period is regarded as one of the greatest of all-time. Under Sacchi, Tassotti was named vice-captain after Baresi, and he won the 1987–88 Serie A title, followed by the Supercoppa Italiana, and consecutive European Cup titles, in 1989, and 1990. In addition, Tassotti won two Intercontinental Cups (1989, 1990) and two UEFA Super Cups (1989, 1990), also reaching the 1989–90 Coppa Italia final. During the 1987–88 season, Tassotti helped Milan to only concede 14 goals in Serie A, finishing the year with the best defence.

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 earned a reputation for being an aggressive and hard-tackling defender as a youngster, with a strong character. At Milan, he developed into a more cautious, composed and consistent player, which led to him being nicknamed "The Professor".

Born in Rome, Tassotti played his first professional season with local club Lazio in 1978–79, where he soon became a first team member the following season, making his Serie A debut on 5 November 1978. During his two seasons with Lazio, he made 41 appearances in Serie A and 47 in all competitions.

Mauro Tassotti (Italian pronunciation: [ˈmauro tasˈsɔtti] ; born in Rome, 19 January 1960) is an Italian manager and former footballer who played predominantly as a right-back. He currently serves as an assistant coach for the Ukraine national team. After making his Serie A debut with Lazio, he went on to play with Milan for 17 years. He won 17 major titles with Milan, including five Serie A championships and three UEFA Champions League tournaments, reaching five finals in total. He is mostly remembered for his role alongside Paolo Maldini, Franco Baresi, Alessandro Costacurta, Filippo Galli and Christian Panucci in the Milan backline under managers Arrigo Sacchi and Fabio Capello, forming what is considered by many in the sport to be one of the greatest defensive lineups of all-time.