When he was growing up Oskar Jenni lived in the old ice rink building in Davos where his father ran a carpentry shop. From there Jenni played ice hockey with HC Davos from 1957 to 1968, winning the Swiss championship in 1958 and 1960, and the Spengler Cup in 1958. He played in 36 matches for the Swiss national team, including four matches at the 1964 Innsbruck Olympics. Jenni retired as a player in 1968 but stayed at the club for another decade working as a coach. He was also a skilled heating technician, air conditioning installer, and plumber.