Career
Kakalov started his career in home town Plovdiv, playing for the local team of Maritsa. The then 18-year-old went to Litex Lovech. Foreign two years he stayed at Litex but only played in three games.
In the 2003-2004 season, Kakalov was loaned to Vidima-Rakovski Sevlievo, then to Belite orli.
From January 2005 to June 2005 Kakalov played for Spartak Pleven.Since the start of season 2005-2006 was playing for Botev Plovdiv
He moved to Belarusian side Dinamo Minsk in 2008. On 8 January 2009 he was loaned for 6 months to Cherno More Varna and then loaned from February 2010 to Olympiakos Nicosia.
On 21 June 2010, he signed with Liga I team Astra Ploieşti as a free agent. Video Game He played as a striker in Championship Manager: Season 03/04.
He was one of the best strikers in that version of game and even ever and was called the "goal machine" by many.