Jesper Olsen began his illustrious footballing career for Næstved IF, and made his debut for the Danish national team in a July 1980 friendly match against the Soviet Union. He had a trial with Arsenal FC in 1978-79, scoring a goal in a reserve team game, and in July 1981 he was recruited by Ajax in the Netherlands.
Since retiring, he has moved to Australia and in 2003 founded and commenced operating the Fun Football Group in Australia, which in 2011 became a part of the Football Star Academy, of which Olsen was appointed Director of Coaching. He oversees the Elite training program, and passes on his worldly knowledge and experiences to new budding football stars. Football Star Academy was instrumental in George Lambadaridis being given a chance to participate in European Football in a move to Club Belgian Club Brugge K.V., and works with Clubs all over Europe such as Panathinaikos F.C. in Greece, and Ipswich Town F.C. in the UK to link Australian talent to international opportunities. In 2009 Jesper Olsen was appointed Assistant Manager of A-League club Melbourne Heart.
Passed penalty: While playing for Ajax, Olsen became well known for his part in the infamous "passed penalty" routine he performed with Johan Cruyff. When Cruyff was awarded a penalty kick in a Dutch Eredivisie league match against Helmond Sport on 5 December 1982, with Ajax leading 1-0, Cruyff passed the ball sideways to Olsen, who returned it to Cruyff, with the Dutchman then slotting the ball past the bemused goalkeeper to make the score 2-0. It was allowed by the referee because the penalty is a direct free kick, so it can also be taken indirectly. During his stay with Ajax, Olsen earned the nickname De Vlo (The Flea) due to his posture and his ability to twist, turn and jump to avoid tackles. He was also called "The Untouchable". The Ajax coach in the 1981-82 season, Kurt Linder, regarded him the most surprisingly talented player in the young Ajax squad, both technically and tactically phenomenal.
Wins: He won the 1981-82 Eredivisie championship in his first season at the club. The next season, 1982-83, Ajax successfully defended the Eredivisie title, and also won the Dutch Cup to complete The Double. Olsen scored twice in the qualification tournament for Euro 1984, including a last-minute equaliser in the 2-2 draw against England. He was selected to represent Denmark at the finals tournament, and played two games, including Denmark's semi-final against Spain. The game ended a draw, but even though Olsen scored in the penalty shootout, Denmark were eliminated when Preben Elkjær missed his shot.
Goals: Olsen moved from Ajax to England in July 1984, joining Manchester United. He scored a total of 24 goals (including a hat-trick against West Bromwich Albion in a 3-0 Football League First Division home win on 22 February 1986) in his five-year spell at the club.
Awards: He collected an FA Cup winner's medal in 1985, when United beat Everton 1-0 in the final at Wembley. He also helped them establish a runaway lead at the top of the First Division in the 1985-86 season, where they won their first 10 league games and remained top of the table until well into the new year.
Final season: Olsen's Manchester United career ended in the 1988-89 season, and he transferred to Bordeaux in November 1988. In his final full season at Old Trafford, United had finished runners-up to Liverpool in the league. His final United goal had come on 12 December 1987 in a 3-1 home win over Oxford United.
Injury: In 1990, he left Bordeaux to play as a wingback for Caen. After suffering a serious injury, he left Caen and retired in 1992, despite being offered the chance to return to English football with Blackburn Rovers and Nottingham Forest.