In 1981, the then-16-year old striker signed with Ajax in 1981. He made his first appearance for the senior side in April 1982, scoring a goal on his debut. He secured a starting position for the 1983-84 season and became the Eredivisie's top scorer that year with 28 goals in 26 league appearances. He remained the league's top scorer for the next three seasons.
While at Ajax, the club won three league titles (1981-82, 1982-83, 1984-85), three Dutch Cups (1983, 1986, 1987), and the UEFA Cup Winners' Cup (1987).
In 1987, Van Basten transferred to Milan. An ankle injury limited his playing time to 11 matches in that first season, but Milan won the Scudetto. Internationally, he led the Netherlands to the 1988 UEFA European Championship as the tournament's top scorer. He won his first European Footballer of the Year award that year.
The following season, he helped Milan to the Serie A title and the 1989 European Cup trophy, scoring two goals in the Final along the way to claiming his second European Footballer of the Year award.
He won his third European Footballer of the Year award in 1992, along with the FIFA World Footballer of the Year award, after leading Milan to yet another Serie A title as the league's top scorer.
His recurring ankle injury ended his playing career in 1993, though he did not officially retire until 1995.