Wasmeier won a total of nine World Cup races, starting with two victories on 9 February 1986, in the Combined and Super-G events at Morzine, France.
His greatest achievement was double gold medals in both Giant Slalom and Super-G at the 1994 Winter Olympics in Lillehammer, Norway. His victory in the Super-G by 0.09 seconds denied the silver medalist, downhill champion Tommy Moe of the U.S., of double gold in the speed events on his 24th birthday. The surprising result of double Olympic gold for Wasmeier at age 30 gained him the title of "Sportsman of the Year" in Germany.
After retiring from competitive skiing, Wasmeier founded the farm and winter sport museum Bauernhof- und Wintersportmuseum Schliersee, and he has remained its curator and patron ever since. The museum provides insight into traditional Bavarian peasant life and aims to preserve old traditions by communicating them to coming generations.
In 2009, Wasmeier shared his passion for building restoration and preserving tradition with an international group of young people through his involvement with the D&F Academy (now The DO School). Wasmeier worked with an international group of young people to restore a 17th-century farmhouse in the German Alps utilizing original materials, traditional tools, wood-crafting and handicraft techniques. He remains involved with the DO School as an advisor and supporter.