He served as an assistant coach of the West Germany national football team when they won the 1990 FIFA World Cup.

[2] In his native country, he played for FC Schalke 04, Eintracht Gelsenkirchen, SSV Hagen, 1.

[3] After finishing his playing career in Canada, Osieck became an assistant coach to Franz Beckenbauer for the Germany that won the 1990 FIFA World Cup.

[3] He then managed VfL Bochum,[4] Fenerbahçe,[5] the Urawa Red Diamonds,[6] and Kocaelispor.

[23] Osieck landed the job of manager of the Canadian men's national soccer team in September 1998.

[29] In the Confederations Cup, Canada lost to Japan and Cameroon and drew Brazil 0–0.

In 2007, he again became the manager of Urawa[6] and led the club to win the 2007 AFC Champions League.

Australia then proceeded to defeat Paraguay 1–0, before suffering a 3–0 loss to Egypt in Cairo.

[citation needed] In January 2011, he led the team to the final of the AFC Asian Cup, before an extra-time loss to Japan 1–0, with Australia conceding just two goals for the entire tournament.

[38] Osieck was widely praised for an otherwise outstanding campaign that included a victory over defending champions Iraq in the quarter-finals, and an amazing 6–0 defeat of Uzbekistan in the semi-finals.

[38] On 30 March 2011, Osieck lead Australia to a shock 2–1 victory over his home country Germany in an international friendly match at Mönchengladbach.

Australia were without their top goal scorer Tim Cahill but managed to score two goals in quick succession midway through the second half with Germany playing a weakened side with coach Joachim Löw playing a younger squad.

In 2013, in World Cup qualifying, Australia defeated Saudi Arabia and Iraq.

[41] On 12 October 2013, after two consecutive 6–0 defeats in friendly matches against Brazil and France,[42] Osieck's contract was terminated with the FFA.