Osiier represented Denmark in 7 Olympic Games between 1908 and 1948. He boycotted the 1936 Berlin Games, to protest against the Nazis.
Osiier won his only Olympic medal in 1912, a silver in Individual Epee, at the Stockholm Games.
Osiier was one of very few athletes to receive the Olympic Diploma of Merit.
He first competed in the 1908 London Olympics, reaching the 2nd round in the individual épée competition (he finished 18th), while Denmark lost in the team competition to France and Great Britain.
Osiier competed in the Stockholm Olympiad in 1912 in all three fencing weapons (foil, épée, and sabre), and won the only medal of his Olympic career. In the individual épée, he finished in 2nd place to capture the silver medal by winning five of seven matches in the finals (Belgian fencer Paul Anspach won the gold medal). At Stockholm, Osiier also was eliminated in the 1st round of both the individual and team sabre competitions. In individual foil, he advanced to the semifinals before being eliminated, and finished 20th.
His next Olympic competition took place in 1920 at the Antwerp Games because the Olympics were cancelled in 1916 due to World War I. There, he competed in three events, and made the finals in all three. He finished in 4th place in the team foil event, 6th place in team sabre, and 8th in the individual foil event.
At the 1924 Paris Olympics, Osiier competed reached the finals in individual foil by winning his pool in the first 4 rounds. In the finals, he was victorious in only one bout (out of six), and finished in 6th place. He also finished in 6th place in individual sabre after winning two of seven matches in the final pool (he again won all his earlier pools). In the team events, Denmark reached the semifinals in foil before losing to Italy and Belgium, and were eliminated in the quarterfinals in épée.
At the Paris Games women’s fencing made its debut, and his wife Ellen Osiier won the gold medal for Denmark at the age of 33 without losing a single bout.
At the 1928 Amsterdam Olympics, Osiier competed in five fencing events (every event Denmark entered). In the individual sabre competition, he reached the semifinals. In individual foil, he won his elimination pool, but was again eliminated in the semifinals after finishing 5th in his pool. Denmark was eliminated in the quarterfinals in team foil, but not because of Osiier, who won 16 of 20 bouts in the competition. In épée he got no further than the semifinals. Denmark was eliminated in the first round of the team épée, although Osiier won five of his eight bouts.
Osiier competed in five events again at the 1932 Los Angeles Olympics. The Danish épée team reached the semifinals before they were eliminated by the United States, despite Osier winning all four of his bouts (the match ended 8–8, but the U.S. had fewer touches received and therefore won). He reached the finals in the team foil event, and placed 4th after Denmark lost to Italy (4–12), France (6–10), and the United States (7–9). Osier also competed in the individual foil and reached the semifinals before being eliminated. In the sabre events, Osier reached the final and placed 7th overall, while the Danish team lost to Hungary (1–11) in the first round (Osiier registered Denmark's only victory in the match).
At the age of 59, Osiier returned to Olympic competition once more, in 1948 at the London Games, 40 years after first participating in the Olympics. He fenced in only one event, the team épée, and Denmark was eliminated in the first round.
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