Osypenko-Radomska was the K-1 500 m champion at the 2008 Summer Olympics. At the 2010 World Championships, she won gold in K-1 500 m and silver in K-1 200 m. She was awarded two bronze medals – in the K-1 200 m and K-1 500 m – at the 2011 World Championships. The following year, she won silver medals in the K-1 500 m and K-1 200 m at the 2012 Summer Olympics in London.