His journalist career began with an internship at the Hamburger Morgenpost.[4] Later, he was an editor and foreign correspondent for the New Yorker Staats-Zeitung, head of a German radio station and staff of the American television ABC in Miami.[4] After his return to Germany in 1966, he was a senior editor at TV the Hessischer Rundfunk, later head of the editorial Television Sports currently at South German Radio. Here he commented on football games for ARD.
From 1971 to 1984, he was one of the moderators of the sports program Sportschau.[5]
Obermann was a senior adviser of the Afghanistan football project sponsored by FIFA.[7] From January until March 2003, he led the Afghanistan national football team.[8][9] From March 2004, he was an honorary member of the Afghan Football Association for his contributions to youth development. After the Indian Ocean tsunami of 2004, he was named by FIFA as technical consultant for the reconstruction program in Sri Lanka, where he worked directly on site.
Obermann helped to found the German American Society of Hollywood Florida in 1964.
Obermann, Holger (1975). Rot-Weiss vor, noch ein Tor (in German). Stuttgart: Thienemann. ISBN3-522-12280-1. OCLC74264256.
—— (1989). Und alle träumen von Pele : meine Erlebnisse am Gambia-River (in German). Stuttgart-Botnang: Consens-Verlag H. Hirschel. ISBN978-3-926729-06-4. OCLC29617532.
—— (2015). Mein Fußball hatte Flügel : Erlebnisse von New York bis Kabul (in German). Wehrheim: Balog. ISBN978-3-95586-001-1. OCLC905354078.