- デンマーク年間最優秀選手 ：1964年
Despite his qualities, Ole Madsen never played in the top-flight Danish championship, but stayed with local lower-league clubs.
Madsen made his senior debut with minor league team BK Stefan in 1954.
In 1958, he moved to Danish 3rd Division team Hellerup IK (HIK).
He helped HIK gain promotion for the Danish 2nd Division for the 1961 season, where the club stayed for three seasons. For the 1964 season, HIK was relegated to the 3rd Division once more.
Despite a low-key club career, Madsen’s international performances for the Denmark national football team got the attention of European professional clubs. As an amateur player, Madsen was a free agent able to sign with any professional club without the need of a transfer fee. In 1963, a contract with Italian club Atalanta Bergamo was hindered by a broken nose and subsequent hospitalization.
Madsen was offered a contract by Spanish club FC Barcelona in 1964, but he turned it down in order to stay an amateur with the Danish national team and HIK in the Danish 3rd Division.
In 1965, Madsen signed a professional contract with Dutch team Sparta Rotterdam, where he enjoyed success.
Madsen stayed three seasons with Sparta, with whom he won the 1966 KNVB Cup.
Madsen scored the only goal, as Sparta beat ADO Den Haag 1–0 in the KNVB Cup final.
In the Dutch Eredivisie championship, Ole Madsen scored a total 22 goals in 71 games for Sparta.
When his contract with Sparta ended in 1968, several big clubs were poised to sign Ole Madsen.
However, Madsen decided to return to Denmark in 1968, in order to play for HIK in the 3rd Division. He tried, unsuccessfully, to move HIK towards his own, more professional ways.
Ole Madsen was forced to end his career with HIK in 1969, following an injury sustained while playing an international game for Denmark.
Within his first year at HIK, Madsen made his debut for the Danish national team in October 1958. He was not selected for the 1960 Summer Olympics, but became a mainstay in the team following that tournament. He was eventually named team captain, and scored six goals in three games against the Luxembourg national football team to help Denmark qualify for the 1964 European Nations’ Cup.
He captained Denmark to a 4th-place finish in the final tournament. That year, Ole Madsen was the first Danish player ever to receive votes in the European Footballer of the Year poll, getting one point and a shared 19th place.
He was subsequently named 1964 Danish Player of the Year.
On 20 June 1965, Madsen scored an extraordinary goal in an international game against the Sweden national football team. The ball fell to him in an inconvenient angle, with Ole himself facing away from goal, but he hit the ball awkwardly with his heel, and it went past Swedish goalkeeper Arne Arvidsson for a 1–0 lead. Denmark eventually won the game 2–1, the first Danish victory against their neighbors in 14 years.
Ole Madsen was then seen as the most popular Danish footballer since Pauli Jørgensen.
When Ole Madsen signed a professional contract in 1965, he was automatically banned from the amateur-only national team.
Following his return to HIK in 1968, Madsen was once more part of the Danish selection. He was the first player to benefit from new rules by the Danish Football Association allowing ex-professionals to re-enter the national team.
He was called up for Denmark in May 1969, and scored two goals in seven games, before injuring his cruciate ligaments in a September 1969 game against the Norway national football team.
This would be the last international game for Ole Madsen. He ended his career with 42 international goals, the third overall goalscorer for Denmark behind Poul “Tist” Nielsen (52) and Pauli Jørgensen (47). Since then, Jon Dahl Tomasson has also overtaken Ole Madsen.