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.[2] In August 1999, Bayern Munich signed Bibishkov.[3][4] 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 his first continental tournament in the UEFA Intertoto Cup.[5][6]
Portugal
In June 2005, he signed with Portuguese Maritimo.[7][8] He would also have a loan spell with division rivals Penafiel the following season.[9]
Litex Lovech
In January 2007, Bibishkov returned to Bulgaria as he was transferred to Litex Lovech.[10] Throughout the season, he played in the 2007–08 UEFA Cup and was named the club's player of the year.[11][12][13] He also added some silverware to the club's trophy cabinet by winning the 2007–08 Bulgarian Cup.[12] Bibishkov was re-signed for the following season where once more he aided the club in successfully defending the Bulgarian cup.[14][15] He would also finish as the club's top goal scorer.[16] After a productive tenure with Litex, he announced his intention to play abroad.[16][17]
Europe
On 6 July 2009, he signed a three-year contract as a free transfer with Romanian team Steaua București.[18][19][20] During his tenure in București, he participated in the 2009–10 UEFA Europa League where he made his debut for the club against Motherwell F.C.[21][22] After only appearing in one match for the Romanian side, he was released after a falling out with the club's management.[23]
In the winter of 2010, he returned to the Portuguese top-tier division to sign with Académica de Coimbra.[24][25]
Israel
In the summer of 2010, he initially was invited for a trial run with Israeli-side Hapoel Ramat Gan Givatayim.[26] After an impressive trial, he signed a one-year contract with an option to play in the Israeli premier league.[27] His tenure in the Middle East was short-lived as his contract with the club was mutually terminated in the winter of 2011.[28][29]
Bulgaria
Following his departure from Israel, he would play the remainder of the season with his former club Pirin Blagoevgrad.[30] His stint with Pirin would only last for six months as he would sign with division rivals Minyor Pernik for the following season.[31] Bibishkov would extend his tenure with Pernik for another season.[32] However, his second season with Pernik was cut short as he requested a release from his contract in November 2012.[33]
He finished off the season with Lokomotiv Sofia.[34] After a season and a half with Lokomotiv, he left the club to seek more playing opportunities.[35]Marek Dupnitsa of the Bulgarian second division would sign Bibishkov for the remainder of the campaign.[36] He would help the club in securing promotion to the country's top-tier league by winning the league title.[37] He re-signed with Marek for the next season but departed during the winter transfer market due to the club's financial troubles.[38]
Canada
In the summer of 2016, Bibishkov played in the Southern Ontario-based Canadian Soccer League with the Brantford Galaxy.[39][40] He would debut for Brantford on May 24, 2016, against Toronto Atomic.[41] Several weeks later he would record his first goal for the club on June 13, 2016, against Scarborough SC.[42] He would assist the club in securing a playoff berth by finishing seventh in the league's first division.[43] Their postseason run ended in the first round after a defeat to FC Ukraine United.[44]
The following season division rivals Scarborough SC recruited him as their player-coach.[45][46] He also played with SC Real Mississauga in the 2018 season.[47] In 2020, he returned to Scarborough where he was selected for the squad that faced Vorkuta in the championship final but was defeated by a score of 2–1.[48]
Managerial career
While in the CSL he transitioned to managing in 2017, where he was appointed in the capacity of a player-coach for Scarborough SC.[45] In his debut season at the helm with Scarborough, he led the eastern Toronto side to a playoff berth.[49] Their first opponent in the playoff tournament was Brantford where Scarborough successfully advanced to the next round.[50] In the second round, the club defeated FC Vorkuta in a penalty shootout that marked the club's first championship final appearance.[51] However, the York Region Shooters would defeat the eastern Toronto club in the championship final by a penalty shootout.[52]
He would also become involved at the grassroots level by serving as the U-11 head coach for the CFA academy.[53][54] In 2018, he became involved with SC Real Mississauga and operated as a player-coach after the academy received a franchise in the Canadian Soccer League.[55][56][57]
In his first season with Mississauga, he led the team to the playoffs by finishing seventh in the first-division standings.[58] Bibishkov would appear in the quarterfinal match against Vorkuta where Mississauga was eliminated from the competition.[58] He would resume his coaching duties for the 2019 season, where the club failed in securing a postseason berth.[59]
After the COVID-19 pandemic in 2020, he left the academy and returned to his native country.[60]
^"Bibishkov discreto no primeiro treino" [Bibishkov discreet in first training]. www.record.pt (in European Portuguese). 2 February 2010. Retrieved 17 January 2024.
^Artzi, Shai (16 August 2010). "הפועל ר"ג: קרום ביבישקוב צפוי לחתום" [Hapoel RG: Krom Bibishkov is expected to sign]. Ynet (in Hebrew). Retrieved 16 January 2024.
^Brenner, Neri (11 November 2010). "הפועל ר"ג: הרכב התקפי לקראת מכבי חיפה" [Hapoel RG: offensive line-up for Maccabi Haifa]. Ynet (in Hebrew). Retrieved 16 January 2024.
^"Локомотив (София) пред раздяла с Бибишков" [Lokomotiv (Sofia) before parting ways with Bibishkov]. Blitz.bg/sport (in Bulgarian). 15 November 2013. Retrieved 16 January 2024.
^"Крум Бибишков започва титуляр за Марек – Стартов състав за мача с Дунав" [Krum Bibishkov starts as a starter for Marek - Starting line-up for the match with Dunav]. Всичко За Дупница, Новини, Коментари, Анализи, Спорт, Страна, Свят, Обяви, Видео (in Bulgarian). 29 March 2014. Retrieved 1 June 2019.