A short trip across the border to play Scotland's perennial bridesmaids and a long journey to Turkey against Istanbul's most progressive club, Burnley fans have already enjoyed what they hope is the start of a long and fruitful European tour.
They are now just two legs away from reaching the Europa League proper with only Greece's most decorated side standing in their way. However, the medal collection is not the only colourful package in Olympiacos' history, expecially in recent years...
Meet Evangelos Marinakis - one of football's most controversial figures
Since the inception of the Greek Superleague in 1927, Olympiacos have won 44 of the 82 league titles, victorious in all but three campaigns since 1996. Yet they enjoyed a torrid season last time out despite lifting the league title on seven consecutive seasons prior to the campaign.
The side from Athens simply could not settle and their President did them no favours at all. Evangelos Marinakis has been at the helm of the club since 2010 but has been nothing short of a controversial figure during his tenure, investigated for match-fixing on several occasions, a major disturbance with former Panathinaikos striker Djibril Cisse and drug trafficking. However, Marinakis has always escaped the charges.
Allegations of match-fixing and bribery have been bubbling issues in Greece, to the point that the government were forced to step in last season and suggest tougher sanctions for failures around stronger stadium security, fan violence (often an issue for Olympiacos) and irregular betting and spot-fixing - Marinakis appeared to be against the proposals that threatened substantial fines and relegation.
"The amateur teams love Olympiacos more than you do"
Marinakis had been used to getting his own way but with several fixtures still remaining of last season, it was clear that it was going to be an unsuccessful campaign for the most decorated side in Greek history. With Olympiacos dwindling in the league behind their two neighbours, AEK and Panathinaikos, and knocked out early in the domestic cup competitions, Marinakis took the unprecendented step of sending all of his first-team players on holiday, promoting the Under-20 squad to the senior ranks.
Marinakis told the senior squad, "I and the rest of the fans have tolerated enough...the amateur teams love Olympiacos much more than you do." The players were also fined the equivalent of £350,000.
However, drastic measures are not uncommon for Marinakis. Despite winning the league in 2017, Olympiacos have seen ten different managers in just two seasons with Marinakis also becoming the majority shareholder of Nottingham Forest during that time.
Oscar Garcia was the man in charge when his players were sent on holiday and he immediately stepped down after just three months as manager - during that time, he was hit on the head by a toilet roll thrown by PAOK fans that forced the contest to be abandoned.
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10 managers in two seasons and 41 transfers in one summer
It perhaps comes as no surprise that there have been wholesale changes in the playing ranks over the summer. 18 players have arrived for a combined total less than six million Euros, whilst a mammoth 23 have departed, most of whom have been released on free transfers.
However, captain and Greece international Konstantinos Fortounis remains after making 100 appearances for the club and will offer a creative threat in attacking midfielder. English fans will recognise full-back Omar Elabdellaoui who has returned from a loan spell at Hull City, whilst defender Roderick Miranda joins on loan from Wolves.
It remains to be seen how a new Olympiacos squad will respond to a dismal campaign last time out. Pedro Martins has taken the reigns and will be hoping for a more prolonged period than his predecessors but history dictates he will be given very little time to succeed.
"A bit like hell"
One thing is for certain - Burnley can expect a hostile atmosphere during the first leg on Thursday evening in Athens. Former Czech Repubic international, Jaroslav Plasil, described the experience as "one of the most intense atmospheres I've ever experienced...a bit like hell for us."
Zlatan Ibrahimovic called Olympiacos supporters "amazing, and a big advantage for the team," whilst Lucas Moura, formerly of PSG and now at Tottenham Hotspur, explained, "it was the most intense and heated stadiums I've ever played in." Last season, a fan invaded the pitch to take a selfie with Leo Messi during a Champions League contest.
Burnley fans will have an experience to remember with this contest.