Wilkins signed with A.C. Milan in the summer of 1984. He later remarked that the most difficult part of adapting to the Italian game was the focus on fitness - the coaching staff made him work to reduce his body fat levels and Wilkins described the result as being in the best shape of his career. The Italian team was struggling during this period, having suffered relegation in the 1981-82 Serie A, and Wilkins was joined by fellow Englishman Mark Hateley (himself replacing another compatriot - Luther Blissett). The only foreign players in the squad, the pair helped the team to victory over rivals Inter in the Milan Derby that October, winning plaudits from Italian press and the club's fans. In his first year there, Wilkins played 28 Serie A games to bring the team to fifth in the league and also won a runner-up medal in the Coppa Italia (having eliminated Inter in the semis).  The following season he remained a key player in Milan's midfield, appearing in 29 league games and scoring two goals - one late goal to salvage a draw at Avellino and another goal the following game against Sampdoria. These were the only Serie A goals of his career. Overall, the team struggled for goals, with Pietro Paolo Virdis's total of 13 making him the club's only goalscorer in double figures that year. The club also suffered off the pitch, with owner Giuseppe Farina absconding to South Africa following accusations of bribery and theft.  In Wilkin's final season there (1986-87), he fell out of the first team structure, following the signing of Roberto Donadoni and the continued presence of both Agostino Di Bartolomei and Alberigo Evani. The team finished fifth in the league, beating Inter twice, in Silvio Berlusconi's first year as owner. Wilkins played 105 games (74 in Serie A) for Milan between 1984 and 1987. Corriere della Sera eulogised him as a "serious and meticulous professional who was immediately appreciated for his long and precise passes".  Wilkins signed for Paris Saint-Germain in the middle of 1987, but this proved to be short-lived: he failed to break into the team ahead of Gabriel Calderon and Safet Susic so he eagerly took the option to signed for Rangers for PS250,000 that November. At the Scottish club he won two league titles and one Scottish League Cup under Graeme Souness. He achieved cult status for his volley in the Old Firm game against reigning champions Celtic in August 1988, giving Rangers the lead in a 5-1 win against their rivals. Despite only playing two seasons for the Glasgow club, he was inducted into their Hall of Fame.

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