In his native country, he played for Schalke 04, Eintracht Gelsenkirchen, SSV Hagen, 1. FC Mülheim and 1. FC Bocholt. However, he never appeared in a top-flight Bundesliga match. Toward the end of his playing career, he moved to Canada to play for Vancouver Whitecaps.

After finishing his playing career in Canada, Osieck became an assistant coach to Franz Beckenbauer for the Germany national football team that won the 1990 FIFA World Cup. He then managed VfL Bochum (Germany), Fenerbahçe S.K. (Turkey), Urawa Red Diamonds (Japan) and Kocaelispor (Turkey) before he landed the job of manager of the Canadian national team in 1999.

Under Osieck, Canada won the 2000 CONCACAF Gold Cup, earning the nickname "Holger's Heroes," a reference to the television show Hogan's Heroes. He worked for FIFA between 2004 and 2006 as chief of their technical department. In 2007, he again became the manager of Urawa and led the club to win the 2007 AFC Champions League. However, he was fired by Urawa on March 16, 2008, after a poor start to the 2008 season.