In his native country, he played for FC Schalke 04, Eintracht Gelsenkirchen, SSV Hagen, 1. FC Mülheim, 1. FC Bocholt and Rot-Weiß Oberhausen. However, he never appeared in a top-flight Bundesliga match. Toward the end of his playing career, he moved to Canada to play for the Vancouver Whitecaps.
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. He then managed VfL Bochum, Fenerbahçe, the Urawa Red Diamonds, and Kocaelispor.
With Bochum, he started on 1 July 1991. His first match was a 2–2 draw against 1. FC Köln. Bochum finished the 1991–92 season in 15th place and were eliminated in the second round of the German Cup. Bochum started the 1992–93 season with a 2–2 draw against Borussia Dortmund. Osieck left Bochum on 2 November 1992 amd had his last match on 31 October 1992, a 3–1 loss to 1. FC Kaiserslautern. Bochum were in last place when Bochum left the club.
Osieck became manager of Fenerbahçe on 1 July 1993. In the 1993–94 season, Fenerbahçe finished in second place in the league and got to the quarter-finals of the Turkish Cup. During the 1994–95 season, Fenerbahçe participated in the UEFA Cup, where they were eliminated in th first round by Cannes. Osieck left on Fenerbahçe 18 December 1994. His final match was a 1–1 draw against Gaziantepspor on 17 December 1994. Fenerbahçe were in fourth place when he left the club.
Osieck was manager of Urawa Red Diamonds between 1 January 1995 and 31 December 1996. The Red Diamonds finished the season in third place and got to the quarter-finals of the Emperor's Cup. During the 1996 season, the Red Diamonds got to the semi-finals of the Emperor's Cup and were eliminated in the group stage of the League Cup.
Osieck was manager of Kocaelispor from 1 January 1997 to 30 June 1998. His first match was a 1–1 draw against Gaziantepspor on 18 January 1997. Kocaelispor finished the season in seventh place. They also won the Turkish Cup. In the 1997–98 season, Kocaelispor participated in the Cup Winners' Cup, where they were knocked out in the second round. Kocaelispor finished the season in 10th place. They were knocked out of the Turkish Cup in the semi-finals.
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.
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. Under Osieck, Urawa finished third in the 2007 FIFA Club World Cup. However, he was fired by Urawa on 16 March 2008, after a poor start to the 2008 season. Urawa were in 17th place when Osieck was sacked.
On 11 August 2010, Osieck was named as the head coach of the Australia, replacing Pim Verbeek, who stepped down as Australia's coach after the 2010 FIFA World Cup. This role also involves actively assisting youth development. His first game as Australia's coach was against Switzerland, with Australia drawing 0–0. His first win as Australia's coach was a 2–1 win against Poland. Australia then proceeded to defeat Paraguay 1–0, before suffering a 3–0 loss to Egypt in Cairo.
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. 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.
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. Australia remained to be the only team to defeat Germany at home or away in 2011. Out of 17 games played in 2011, Australia achieved 12 wins, three draws and two losses.
In 2013, in World Cup qualifying, Australia defeated Saudi Arabia and Iraq.
On 18 June 2013, Osieck precipitated a bout of conniptions from Australian talisman Tim Cahill and enraged Australian fans by substituting him in the 78th minute of the 2014 World Cup Qualifier against Iraq. His decision was to be vindicated, however, with the tactical substitution of Joshua Kennedy scoring the decisive goal in the 83rd minute and hoisting Australia to a third successive World Cup berth.
On 12 October 2013, after two consecutive 6-0 defeats in friendly matches against Brazil and France, Osieck's contract was terminated with the FFA.As of 9 January 2017.
TSYD Cup: 1994–95
Turkish Cup: 1996–97
Urawa Red Diamonds
AFC Champions League: 2007
CONCACAF Gold Cup: 2000
AFC Asian Cup: Runners-up: 2011