Sliven reached its peak in 1990, when the team managed to win the 1989–90 Bulgarian Cup, its only major trophy to date.

Through the years the leading club in Sliven had different names - Asenovetz, DNA, General Zaimov, Mlada Gvardia etc.

Over the next few years, the club went into a deep crisis, and was relegated to the regional football groups, eventually culminating in bankruptcy and dissolution.

In 2005, the club finally earned promotion back to the second level of Bulgarian football, returning to professionalism.

In their first year after returning to the elite, season 2008-09, OFC Sliven managed to finish in 12th place, thus avoiding relegation.

This first season in the elite was under the management of Georgi Dermendzhiev, who would later successfully coach Ludogorets Razgrad and qualify the team two times for the UEFA Champions League group stage.

The team largely struggled with their performance, mainly due to the fact that many top players left the club after they were relegated.

The team began experiencing serious financial problems, which affected their results, but more importantly, their ability to play professional football.

On February 26, 2013, the Bulgarian Football Union suspended Sliven's participation in the B Group, as the team could field at most seven senior players.

It was revealed that club legend Yordan Letchkov was the key man behind the success of the team once more, similarly to his financial backing of OFC Sliven 2000.

One of the nicknames of OFC Sliven 2000 is Voivodite which means "Slavic title that originally denoted the principal commander of a military force".

Note: Flags indicate national team as defined under FIFA eligibility rules; some limited exceptions apply.

Currently Hadzhi Dimitar is part of a big multifunctional sports compound, still under development - at completion featuring hotel, restaurant, 2 training grass pitches, tennis courts, swimming pool.

The athletic track of Hadzhi Dimitar is meeting all requirements of IAAF for hosting international competitions.