Osieck landed the job of manager of the Canadian men's national soccer team in September 1998. His first match didn't come until 1999 when Canada played to a 1–1 draw against Northern Ireland. His first two wins came against Guatemala when Canada won 1–0 on 28 May 1999 and 2–0 on 1 June 1999. In 2000, Canada participated in qualifying for the 2002 FIFA World Cup. Canada eliminated Cuba. However, Canada finished third behind Trinidad and Tobago and Mexico and were eliminated from the tournament. Under Osieck, Canada won the 2000 CONCACAF Gold Cup, earning the nickname "Holger's Heroes," a reference to the television show Hogan's Heroes. They defeated Colombia in the final. In 2001, Canada participated in the Confederations Cup. In the Confederations Cup, Canada lost to Japan and Cameroon and drew Brazil 0–0. Canada finished in last place in Group B. In 2002, Canada participated in the Gold Cup where Canada defeated South Korea in the third place match. Osieck resigned in September 2003. His final match was a 2–0 loss to Cuba in the 2003 CONCACAF Gold Cup.