Jakob Piil was born in Virum, Copenhagen. He started his career as a track racer, riding six-day races with shifting partners, including the Danish riders Michael Sandstød, Tayeb Braikia, and Jimmi Madsen. In 1997 he signed up for the RDM professional cycling team, getting only a handful of top-ten results in his first year as a pro. He moved to Danish Team Acceptcard in 1998, where he got the first, minor, victory of his career at the GP Skive in 1998. 1999 was his professional breakthrough with many good results, and a meriting win of the USPRO Championship. In 2000, he switched to Team CSC, back then known as Team Memory Card – Jack & Jones.

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