In the European Champions Cup in 1967 the club faced FK Sarajevo Yugoslavia.

It could be said that the club did not transition well from the era of amateur to semi-professional football in Cyprus beginning in the early 1980s mainly for the reasons mentioned above.

In the 1968–69 season, Olympiakos with Englishman Eric Brookes as manager won the championship for a second time, collecting 52 points the same number as AC Omonoia.

After the end of the first round, however, Kouloumbris was sacked due to the bad defensive record of the team, despite the team being in 3rd place.

It also in the past had an orchestra, choir and camping divisions; the latter explaining why the club's badge has a tent on it. The club tried to re-organise itself and to return to the top flight as quickly as possible. Seraphim who was offering his services for free, totally reorganised the club for the new season.

In both the 1983–84 and 1997–98 seasons the club had spent just one season in the second tier of Cypriot football, only to win the Cypriot Second Division title each time and return to the Cypriot First Division. At the end of the first round the club was in 11th place just above the relegation spots, falling to 12th place after 21 games and in the battle to survive relegation.

Papadopoulos was released by mutual consent at the end of February 2012 with the club in the cup quarterfinals but fourth from bottom in the league, although defensively the club was marginally better it lost its attacking flair and pressing style with majority ball possession and suffered from conceding goals right after scoring.

On 24 July the contract with Chrysis Michael was terminated by mutual consent and ex-captain Nikolas Nicolaou took over as caretaker manager until 12 August 2016 when Savvas Paraskeva took over the helm.

Olympiakos has also taken part in all three European competitions. With around 1.6 million Euro of total legacy debt (old players, banks, creditors and the state) however, the future of the club was looking all the more uncertain. the second round and earned the opportunity to avoid relegation in the third round. Olympiakos was champion however because of the better goal difference. In all these European games Olympiakos was forced to play both games away from home as at the time the Cypriot football stadia did not meet the European regulations. From the senior players only captain, defender Nikolas Nicolaou and midfielder, vice-captain Kyriacos Polycarpou remained. Championship, in the 1967–68 season, something which recurred twice more, in 1969–70, and in 1971–72, rendering the club the only Cypriot team that participated three times in the Greek National 1st Division Championship.

His first signings were Cypriot right back Paris Psaltis, Cameroonian defensive midfielder Eyong Enoh, central defender Sambinha from Guinea-Bissau, Cypriot defensive midfielder Giorgos Economides, goalkeepers Pavol Bajza from Slovakia and Mario Kirev from Bulgaria, Portuguese left back Kiko, Cameroonian winger Fabrice Kah, Cypriot defensive midfielder Evangelos Kyriacou, Cypriot Striker Panayiotis Zachariou, Venezuelan midfielder Rafael Acosta, Brazilian Forward Azulão and Ghanaian centre back Ousmane Sidibé. Even when the club fell to the Second Division between 2008 and 2010 due to economic problems, 300 supporters would follow the club to even the most remote village of Cyprus, with home attendance varying between 500 and 750.

Olympiakos later played in the same competition in 1971 and met Feyenoord of the Netherlands and lost 8–0 and 9–0. FIFA had imposed an embargo on signing new players over 18, so the club had to compete in the first division with its existing squad until January. Chairman Petros Savva resigned and Manager Marios Constantinou left making way for old Olympiakos Nicosia defensive midfielder Costas Seraphim.