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  • Writer's pictureStephen Kountourou

Olympiakos 1998/99: The BitterSweet Adventure

For many clubs competing on the greatest stage, a run in Europe, let alone winning a major competition, feels like an unattainable dream at times. It takes the stars to align with the right players, the right manager, and sheer determination for a plucky underdog to go far in an elite tournament. In the past we have seen sides such as our eternal rivals Panathinaikos reach the final of the old European Cup in 1971, APOEL’s more recent run with a team worth fewer than one million Euros to the last eight of the Champions League in 2011/12, and the even more extreme case of Ukrainian side FC Dnipro, who went all the way to the Europa League final in 2014/15.

Our Olympiakos had just that when they competed in the 1998/99 edition of the UEFA Champions League, and went all the way to the quarter finals before experiencing the heartbreak of being knocked out with minutes to go against Juventus. With manager Dusan Bajevic and co., Thrylos gave our amazing supporters a season in Europe to remember and that is what I will be writing about. In a rather quiet offseason featuring a lot of international football, thanks to the Euros, I'll be taking a look back at Olympiakos’ greatest European run to date, including how they performed before the 1998/99 campaign. I will then highlight Thrylos’ fantastic group stage run before standing toe-to-toe with Italian giants Juventus in the last eight of the competition.

Record in Europe Prior

The Erythrolefkoi made their maiden campaign into European football way back in the 1959/60 Preliminary Rounds, when the Greek side drew AC Milan. An admirable 2-2 draw was swiftly followed up with a 3-1 loss in Italy and it was an early exit for Olympiakos; not the worst European Cup performances for the debutantes.

A couple of years later Thrylos would claim their first and only continental trophy by winning the 1961/63 Balkans Cup, going all the way to the final and defeating Bulgarian side Levski Sofia over a two-legged final before the third match on natural ground deciding the tie. For more detail of this historic win for our side, check out the last blog I did about this rather obscure part of Olympiakos’ coveted past.

Back in the official UEFA competition, Olympiakos would progress to the next round of a major tournament for the first time as they reached the second round of the UEFA Cup Winners Cup in 1963/64. After beating Polish side Zagłębie Sosnowiec over three matches in Round One, Lyon lay in wait for the Greek side in Round Two. After being well beaten in France 4-1, Thrylos did end their European season with a respectable 2-1 victory but it was not enough to see them through to the next round.

From that point, Olympiakos did consistently reach the second round of the Cup Winners Cup and the UEFA Cup, but it would not be until 1974/75 when Thrylos would finally go to the next stage of the European Cup. After defeating Scottish side Celtic after two legs, Anderlecht was drawn to play Ethryolefkoi. A 5-1 thrashing was followed by a 3-0 victory in Piraeus but it was not enough to see Olympiakos progress, and they bowed out of the tournament 5-4 on aggregate.

During the ‘80s, supporters of the portside club saw their team progress to the next round of European competition in 5 of 10 possible campaigns. The end of the decade culminated in Thrylos reaching the Third Round for the first time in the club’s history during the 1989/90 edition of the UEFA Cup. After edging past Yugoslavian side FK Rad and Austrian team First Vienna, they were eventually knocked out themselves by French side Auxerre.

Two seasons later, Olympiakos reached the quarter finals of the Cup Winners Cup. In the first tie against Ukrainian side Chornomorets Odesa, Thrylos overcame a 0-1 loss in Piraeus to smash their opponents away 0-3. Thrylos then went on to knock out Monaco in a shock result to excite the Piraeus faithful. Atletico Madrid sadly ended our European journey in the end after comfortably dumping the Greek side out after two legs.

After being a constant in the UEFA Cup throughout the 90s, Olympiakos returned to Europe’s biggest competition after 10 years away, this time in the new UEFA Champions League. Upon qualifying at the expense of Belarusian side MPKC Mozyr, Thrylos entered the group stages where they struggled at times but finished third in a group containing Real Madrid, Porto, and Rosenborg. Highlights of the group included a 1-0 victory over the Portuguese side thanks to a goal from one Stelios Giannakopoulos. Fans of Erythrolefkoi would not have to wait long for a run in the elite competition.

Cypriot Obstacle and Topping the Group

Much like the season before, Olympiakos were placed against Cypriot side Anorthosis Famagusta in the Champions League qualifying round. Thrylos comfortably overcame Kuanolevkoi, first 2-1 in Piraeus and followed by a 2-4 victory on the road in Cyprus, to reach the group stage for the second consecutive year. The Piraeus side was placed in Group A which contained the previous season’s opponents Porto, Croatia Zagreb (now Dynamo Zagreb), and Dutch giants Ajax, a tough group where arguably anyone could have topped the group or finished bottom after six games.

As it transpired, it was our legendary club that managed to do the former. Matchday 1 involved a tough trip to Porto where they were hosted by, well, Porto. With only 8 minutes of normal time to go, Olympiakos found themselves 2-0 down and on the verge of an opening defeat in the competition. In a miraculous recovery, Thrylos were able to come back and draw 2-2 thanks to goals from Serbian Cypriot legend Siniša Gogić and that man Stelios Giannakopoulos.

Erythrolefkoi continued their European campaign strong with a win at home in front of a packed Karaiskakis crowd 2-0 against Croatia Zagreb, with the goals coming in both halves from Alexis Alexandris and Gogić repetitively. It would be followed by a second win in a row in a huge 1-0 victory against former champions Ajax with a second consecutive goal for Alexandris.

The return match in Amsterdam did not go as smoothly for Thrylos as they suffered their first loss of the group against the home side 2-0. Thankfully Bajevic's men were able to bounce back and defeat Porto in Piraeus 2-1, thanks to a third goal of the group from Gogić and a second from legendary wide man Predrag Đorđević. With that win, Olympiakos were guaranteed top two in the group but still not assured a quarter final place.

As the final game of the group approached, all Thyrlos needed at least a draw to advance to the knockout stages. Thankfully Olympiakos did just enough as they managed a 1-1 draw away in Croatia, courtesy of a second half goal from Giannakopoulos, who had helped his side reach the quarterfinals of the Champions League for the very first time.

Quarter Finals and Late Heartbreak

Upon this milestone in the history of Olympiakos, standing in between them and the semifinal were Italian giants Juventus. With the first leg being played in Turin, this would be no easy task for Thrylos, especially as they had not won an away match during the group stages. Their best hope was to at least score and take an away goal back home, giving them a better chance of overcoming their superior opponents.

As half time drew closer in a packed Stadio Delle Alpi, the deadlock was broken by poacher Pippo Inzaghi, putting the old lady ahead and making Olympiakos’ task that much harder. After Antonio Conte doubled the hosts’ lead, Thrylos won a penalty in the dying moments of the game, which was well taken by Andreas Niniadis. Despite the loss there, Olympiakos were still very much in the tie going into the return leg.

With a huge 75,000-person Olympic Stadium crowd acting as the 12th man, it was the perfect atmosphere for Olympiakos to try to turn the tie on its head and reach their first ever Champions League semi finals. The match started perfectly for the Piraeus side as Gogić popped up once again with an early goal, making it 2-2 on aggregate and putting Thrylos through thanks to the away goal. For the rest of the match, Olympiakos attempted to hold on to their slim lead until the final whistle. They came within five regular minutes of achieving their goal, but football sadly can be a cruel game.

In the 85th minute, Conte popped up again and equalised, putting Juventus back in control of the tie with Olympiakos having hardly any time to respond. The Italian midfielder had crushed the team’s and fans’ dreams of reaching the last four of a major European competition and Thrylos sadly bowed out after coming so close to a now unattainable dream. Reality set in and Olympiakos waved goodbye to the Champions League once again, only this time it was an even more bitter pill to swallow.


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