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While in the CSL he made the transition to managing in 2017, where he was appointed in the capacity of a player-coach for Scarborough SC. Bibishkov achieved a notable result in his first year by reaching the CSL Championship final, where they were defeated 5–4 in a penalty shootout against York Region Shooters. He was associated with CFA academy, where he served as the U-11 head coach. In 2018, he became involved with Real Mississauga SC, and operated as a player-coach after the academy received a franchise in the Canadian Soccer League.

He went abroad once more to play with Hapoel Ramat Gan Givatayim F.C. in the Liga Leumit. In 2011, he returned to Bulgaria to play with Pirin Blagoevgrad, Minyor Pernik, Lokomotiv Sofia. In 2014, he assisted Marek Dupnitsa in securing promotion by winning the Second Professional Football League. He went overseas in 2016 to play with the Brantford Galaxy in the Canadian Soccer League. The following season he was recruited by Scarborough SC as a Player-coach. He also played with Real Mississauga SC in the 2018 season.

In January 2007, Bibishkov was transferred to Litex Lovech, with whom he won the 2008 Bulgarian Cup. In December 2008, he was named the 2008 Footballer of the Year of Litex, and participated in the 2007–08 UEFA Cup. On 6 July 2009, he signed a three-year contract as a free transfer with Romanian team Steaua Bucureşti. During his tenure in Bucureşti he played in the 2009–10 UEFA Europa League. On 3 February 2010, Bibishkov signed a one-and-a-half-year contract with Portuguese club Académica de Coimbra.

He started his career in his home town of Blagoevgrad where he represented the local team Pirin. He played for Pirin Blagoevgrad in six matches, scoring one goal. In August 1999, Bayern Munich signed Bibishkov. In July 2000, he returned to Bulgaria, signing a contract with Levski Sofia. In June 2002, Bibishkov transferred to Marek Dupnitsa, where he played in the UEFA Intertoto Cup. In June 2005, he signed with Portuguese Maritimo. However was loaned out to FC Penafiel the following season.

Krum Georgiev Bibishkov (Bulgarian: Крум Георгиев Бибишков ; born 2 September 1982) is a Bulgarian former footballer, and currently serves as a head coach and club representative for Real Mississauga SC in the Canadian Soccer League.