Kolukanova made her Olympic debut as a 19-year-old at the 2000 Summer Olympics in Sydney where she competed in the women's 50 m freestyle. She reached the semifinals by winning the swim-off against European champion Mette Jacobsen of Denmark and Ana Belén Palomo of Spain. She set a new Estonian record in two consecutive swims, first in the prelims (25.96) and then in the three-person swim-off a few hours later. Followed by an evening session, Kolukanova finished her semifinal run with a time of 26.03, just seven hundredths of a second (0.07) outside her record.