Dynasty Cup
Kalkanov started his career with Lokomotiv Plovdiv. He took part in the 1985 FIFA World Youth Championship with Bulgaria, making three appearances in that tournament. Kalkanov then played in Hong Kong for Instant-Dict and Happy Valley, and in Malaysia for Selangor and Kelantan. While in Hong Kong, Kalkanov won the Hong Kong Footballer of the Year award in 1998, becoming the first non-Hong Konger to win the award. He played for the Hong Kong League XI at the 1998 Dynasty Cup, 2000 Guangdong–Hong Kong Cup and the Carlsberg Cup in 2000 and 2001.