Some of the greatest players in European basketball have played for Olympiacos over the years including: Charlie Yelverton, Carey Scurry, Žarko Paspalj, Giorgos Sigalas, Dragan Tarlać, Walter Berry, Panagiotis Fasoulas, Roy Tarpley, Eddie Johnson, Alexander Volkov, David Rivers, Artūras Karnišovas, Dino Rađja, Theo Papaloukas, Alphonso Ford, Tyus Edney, Arvydas Macijauskas, Miloš Teodosić, Nikola Vujčić, Josh Childress, Linas Kleiza, Rašho Nesterović, Kostas Papanikolaou, Kyle Hines, Acie Law, Georgios Printezis and Vassilis Spanoulis.

[7] The second title did not come until 11 years later, in 1960, and allowed the Reds for the first time to qualify for the European Champions Cup (now called EuroLeague) (1960–61 season), which was their first ever participation at the European-wide level.

Although the 1970s was the most successful decade for the team up to that time, the 1980s marked a low period for the Reds, who did not manage to play a major domestic role, being outshined by the up-and-coming superpowers from Thessaloniki, Aris and PAOK.

However they did not manage to qualify for the 1993 FIBA European League Final Four in Piraeus, Athens which was held at their home court, Peace and Friendship Stadium, as they were eliminated by Limoges CSP in the quarter-finals with 2–1 wins, after a breathtaking third game in Palais des Sports de Beaublanc (58–60), which was decided in the last seconds after an off-balance two-points shot by the Slovenian star Jure Zdovc.

The following year, Olympiacos had a top-class roster with players like Roy Tarpley, Žarko Paspalj, Dragan Tarlać, Panagiotis Fasoulas, Giorgos Sigalas, Milan Tomić, Franco Nakić and Efthimis Bakatsias, and reached the FIBA European League Final Four in Yad Eliyahu Arena, Tel Aviv for the first time in their history.

After an impressive run in the top 16, achieving significant away wins for the first time in the European history of the club against Real Madrid Teka (58–57 in Palacio de Deportes) or against Benetton Treviso (79–73 in Palaverde) and a newfound home victory by 18 points difference against FC Barcelona Banca Catalana (82–64), the "Reds" qualified as group winners (11–3 record) for the quarter-final playoffs where they faced the ranked fourth of the group B, the Italian champions Buckler Beer Bologna of Yugoslav superstar Sasha Danilović and eliminated them hardly with 2–1 wins.

The aim of the Greek Cup extinguished from the beginning after the defeat by Panathinaikos with the strangeness 40–42 in the knock-out match that held in the Sporting Indoor Hall because Olympiacos was punished for the events that take place in the fifth final of the last season play-offs against PAOK.

In Europe the team launched their obligations with a resounding victory (77–42) at Abdi İpekçi Arena against Efes Pilsen, continued with some extended victories at home (101–69 against risky Cibona, 84–53 against the decadent European champions of 7up Joventut, 89–64 against Buckler Beer Bologna), achieved the classical double win against Bayer 04 Leverkusen of Dirk Bauermann, did the classical double defeat by the Limouzo of Božidar Maljković, crashed (99–78) FC Barcelona Banca Catalana in SEF and eventually qualified as second from the group B with the homecourt advantage in their pocket.

Olympiacos eliminated CSKA Moscow with 2–1 wins in the quarter-final playoffs and reached their second FIBA European League Final Four in Pabellón Príncipe Felipe, Zaragoza, facing again their eternal enemies Panathinaikos in the semi-final.

[9] Five players scored in double digits (Rivers 16 points, Tarlać 14, Nakić 12, Berry and Sigalas 10 each) and led Olympiacos to their fourth consecutive Greek Championship in front of their ecstatic fans, who celebrated the title and the historic win in a euphoric frenzy at Peace and Friendship Stadium.

In the second match, at Peace and Friendship Stadium, in front of 17,000 ecstatic Reds fans, Olympiacos beat Panathinaikos once more by a score of 65–57 and advanced to the Final Four in Rome.

The thousands of Olympiacos fans who filled Palaeur arena, were quick to sing that, "in Rome, in the final, we lifted the European title" (Greek: Στη Ρώμη και στον τελικό, σηκώσαμε Ευρωπαϊκό).

Olympiacos played in the round of 16 of the EuroLeague, with a home court advantage against Partizan in a three-game series, but they lost both matches in Athens and Belgrade and the European Champions suffered an early and disappointing elimination.

The score of that game gave the Reds the aggregate advantage in case they finished on the top of the group along with their rivals, a scenario that looked highly probable.

Olympiacos also shined in its domestic competition, as the Reds made it to the Greek League finals for the first time in five years by surviving a thrilling five-game series against Maroussi.

In the 2006–07 season, with the signings of head coach Pini Gershon and Arvydas Macijauskas, the Reds were one of the favorites to claim the EuroLeague crown, but they did not manage to qualify to the Athens Final Four.

In the third match, Olympiacos lost 86–85 in overtime, with the Reds complaining furiously against the referees, who did not call a clear foul against Scoonie Penn with only 3 seconds left in the game.

The 2008–09 season began with high expectations due to a big budget and a great roster with players like Josh Childress, Theo Papaloukas, Miloš Teodosić, Nikola Vujčić, Ioannis Bourousis, Lynn Greer, Panagiotis Vasilopoulos, Sofoklis Schortsanitis and Georgios Printezis.

Despite the loss in a match that could have easily gone either way, the team's great effort and the club's return to the elite of European basketball were clear signs of their future success.

In the quarter-final playoffs, the faced the Polish champions Asseco Prokom and eliminated them with 3–1 wins, reaching for the second consecutive season the EuroLeague Final Four which was held in Paris.

In the Greek Championship finals, the club lost 3–1 wins to Panathinaikos after an intense third game that would have put them ahead 1–2, with the Reds having again huge complaints over the referees' performance.

In July 2010, Olympiacos offered a three-year contract worth €13,200,000 euros gross income to the famous Greek guard Vassilis Spanoulis, and came to an agreement with the player.

The great Serbian coach Dušan Ivković agreed with the club, and with a roster of players such as Miloš Teodosić, Vassilis Spanoulis, Theo Papaloukas, Loukas Mavrokefalidis, Jamon Gordon, Rasho Nesterović, and Ioannis Bourousis, Olympiacos became a favorite to win the 2010–11 Euroleague.

In the Greek League, Olympiacos took the first place in the regular season, but despite earning home-court advantage for the finals, they lost the first game at home, and suffered a 3–1 defeat in a best-of-five series, as they let a chance at the championship slip away.

The team that the press thought might not even qualify for the Top 16, improved dramatically over the course of the season, and under the great performances of Vassilis Spanoulis, Georgios Printezis, Kostas Papanikolaou, Kyle Hines, Joey Dorsey, Pero Antić, Acie Law, Kostas Sloukas, and Vangelis Mantzaris, Olympiacos managed to reach the 2011–12 Euroleague Final Four in Istanbul, after breaking the home-advantage of the Italian champions, Montepaschi Siena, winning with a 75–82 score in the first game of a best-of-five series in Italy, in a reversal of the previous season's quarter-finals.

Stratos Perperoglou, Giorgi Shermadini and the two-time NBA Champion Josh Powell joined the team to replace Marko Kešelj, Joey Dorsey, and Lazaros Papadopoulos.

Olympiacos managed to rally from a 15-point second-quarter deficit to win the game, with an 82–72 scoreline, thus securing the chance to defend their European crown in the Final Four.

After rolling past CSKA Moscow with a smashing 69–52 win in the semi-final,[18] they managed to beat Real Madrid 100–88 in the final at London's The O2 Arena, roaring back from a 17-point deficit in the first quarter, and scoring 90 points in the remaining three-quarters.

[38] However, Olympiacos proceeded to legal action, asking from the high council for the solution of athletic disputes to void the last matchday of the regular season, pointing out that all referees assignments were illegal, thus the playoffs were postponed for one week.

In October 2009, Olympiacos visited the United States on their 2009 NBA tour, and played against the San Antonio Spurs, at the AT&T Center, and against the Cleveland Cavaliers, at Quicken Loans Arena.