Chipilov started training his abilities at Levski Sofia's Youth Academy.
Chipilov joined Dynamo's second team in 2004 and played in the Ukrainian First League for a few seasons.
He was loaned to Bulgarian sides Botev Plovdiv and Chernomorets Burgas during 2007 and 2008.
On 19 June 2009 Chipilov began a trial-period at his former club Levski Sofia.
This biographical article related to association football in Bulgaria, about a midfielder, is a stub.