The team was sold in 2000 to prominent Greek businessman Evangelos Mytilineos for almost €3,500,000 (1.18 billion drachmashttp://archive.enet.gr/online/online_text/c=115,dt=13.11.2005,id=52291600 ). Despite the acquisition of many promising players during the first summer, the 2000–2001 campaign didn't have the expected results, with the club finishing in 5th position, out of European qualification spots. However, Iraklis managed to progress to the 2nd round of UEFA Cup, where they achieved a memorable (although without any effect) win over 1. FC Kaiserslautern in Fritz-Walter-Stadion. Next summer, Mytilineos's first move was to sell the highly rated striker and fans' favorite Michalis Konstantinou to Panathinaikos, setting a new record for the highest fee received for a domestic transfer. That move worsened the relationship between the new owner and the fans, while it clearly weakened the club, since Konstantinou was not replaced. Manager Giannis Kyrastas, who was widely considered one of Greece's bests, was replaced by previous coach Angelos Anastasiadis who in his second tenure managed to qualified once again for the UEFA Cup on a very small budget. In 2004, Mytilineos announced his desire to leave the team and therefore sell it to Giorgos Spanoudakis (a friend of his from their school years, who used to be first vice-president of the club), for just €1, since the team was heavily in debt. Spanoudakis initiated a series of expensive but unsuccessful deals like Polish international Cezary Kucharski and Serie A veteran Giuseppe Signori, driving the team close to bankruptcy. He later tried to get rid of the team by selling it to yet another unknown businessman named Dimitris Houlis, who had been a president of Akratitos F.C. After a 5-month period during which Houlis controlled the team, the Greek football commission finally annulled the transfer, raising questions in the media regarding its handling of the previous one between Mytilinaios and Spanoudakis, too.
