In 1991, Olle won his first Estonian championship over 30 kilometers classic. He first appeared internationally in 1994 when he won the Tartu Maraton , a ski marathon in the Worldloppet series. He had his first appearance at an international championship a year later at the Nordic World Ski Championships in 1995 in Thunder Bay , where he was able to achieve 37th place over 30 kilometers classic and 65th place over 10 kilometers classic. Two years later he was in Trondheim 30th over 50 kilometers classic and 64th over 10 kilometers classic. The classic specialist scored his first points in the cross-country skiing world cup in the 1997/98 season . In Davos he finished 27th over the distance of 30 kilometers. At the 1998 Winter Olympics in Nagano he was 17th over the 30 kilometers and 37th over the 10 kilometers in the classic technique. He could not confirm these results at the Nordic World Ski Championships in Ramsau in 1999 and only finished 35th and 36th over the 10 and 50 kilometers classic. In the following year, Olle concentrated on the FIS Marathon Cup and was the first Estonian to win the Wasalauf . He won the overall ranking of the FIS Marathon Cup well ahead of Staffan Larsson . He was also able to convince in the FIS Marathon Cup in the 2000/01 season. He took second place at the Finlandia-hiihto and was third overall. At the Nordic World Ski Championships in Lahti in 2001 , he was 35th over 15 kilometers classic. Also that season he won the Tartu Maraton for the second time. He was able to confirm his good performance over the long distances in 2002 when he was able to take 18th place over the 50 kilometers at the 2002 Winter Olympics in Salt Lake City and was only beaten by Juan Jesús Gutiérrez at the Marcialonga ski marathon . At the Jizera Mountains Run , he won over 50 km classically. In the 2002/03 season he achieved third place in the Jizera Mountains and further top ten placements in the FIS Marathon Cup. This year he finished seventh in the overall ranking. The following year he achieved his best World Cup placement when he was able to fight for eighth place over 70 kilometers in Val di Fiemme . At the Wasalauf and the Jizera Mountains he came second. At the König-Ludwig-Lauf and in the overall ranking of the FIS Marathon Cup, he just missed the podium in fourth. Olle had his last appearance at an international championship in 2005 at the Nordic World Ski Championships in Oberstdorf in 2005 . With the Estonian relay, he finished ninth. This season he finished second at the Kangaroo Hoppet and the Jizera Mountains and won the Tartu Marathon for the third time. In 2006, Olle won his last podium finishes in the FIS Marathon Cup at the Birkebeinerrennet and the Isergebirgslauf with third place and finished ninth overall at the end of the season. In the following year he played his last marathon competitions, in which he was able to place himself in the top ten several times. His last season in the FIS Marathon Cup he finished ninth in the overall standings again.
After the doping incident involving Andrus Veerpalu , Olle replaced Mati Alaver as coach of the Estonian national cross-country skiing team in the 2011/12 season . However, after the season was more than disappointing, the collaboration ended after just one season.
successes
Victories in Worldloppet Cup races
Note: Before the 2015/16 season, the Worldloppet Cup was still called the Marathon Cup .
Estonia
Halls - Mora