“Big Sam loved to throw a wrench in the party,” Stelios Giannakopoulos reminisces as he recalls Bolton’s battles against Arsène Wenger’s Arsenal in the Premier League. It was a stark contrast of styles, with the swift passing and attacking prowess of Robert Pires, Dennis Bergkamp, Thierry Henry, and co. clashing with the direct, physical approach of Allardyce, spearheaded by Kevin Davies. The two teams will face off again at the Emirates Stadium on Wednesday night in the Carabao Cup, but the balance of power has shifted dramatically. Since Sam Allardyce’s tenure, Bolton has plummeted from Premier League stalwarts to the edge of extinction. Now back in League One, they are once more aiming to pull off an upset.

Giannakopoulos was part of Allardyce’s eclectic mix of foreign talent that turned into unlikely cult heroes. From Jay-Jay Okocha and Youri Djorkaeff to Iván Campo and Nicolas Anelka, Bolton’s early 2000s squad was a vibrant melting pot of cultures, all united by a desire to challenge the elite. Arsenal managed to win four out of 12 league encounters against Allardyce’s Bolton, a record that fell short of their lofty Wenger-era standards. “I relished beating Arsenal more than any other team during my time at Bolton,” Allardyce penned in his autobiography. “We really got under their skin, and Arsène Wenger despised us.”

During Bolton’s heyday, 28,000 fans would pack into the then-Reebok Stadium, hoping to see their team upset the likes of Arsenal, Manchester United, and Chelsea. “It was a daunting place to visit,” recalls former Arsenal defender Justin Hoyte. “No one wanted to play there—it was just a nightmare. Bolton’s style of play was unfamiliar and uncomfortable for Arsenal, making it a tough environment. It always felt like we were playing night games there, cold and windy, with rain pouring down. It was one of those matches where you just wanted it to end.”

Even Arsenal’s Invincibles couldn’t escape a draw at the Reebok Stadium in their final match before Christmas. No matter how high the confidence in north London, seeing Bolton on the fixture list would bring a hint of unease to the dressing room. The better Arsenal performed, the more significant Bolton’s points haul felt.

“Allardyce thrived on making a statement, especially in the big games, and our mentality was always the same,” Giannakopoulos recalls. “If you couldn’t handle the pace and physicality, you had no chance of winning the championship. We exploited these weaknesses, particularly against Arsenal, and managed to secure several victories.” Giannakopoulos scored in three home wins against Arsenal in league and cup matches, ironically becoming Bolton’s chief tormentor despite not being the most physically imposing player. “The only thing I remember is them crossing the ball, and I missed a header at the back post, allowing someone to score over me,” Hoyte says, forgetting it was Giannakopoulos who nodded in.

Giannakopoulos reflects, “We had built an incredible atmosphere, a fortress, making it incredibly tough for any team to visit. That’s a testament to our fans and to us, as we consistently delivered performances that were both convincing and enjoyable to watch, combining good football with results.”

Arsenal’s discomfort extended beyond the pitch. Wenger frequently engaged in heated exchanges with the fourth official about how his players were being treated, and in one match, he refused to shake Allardyce’s hand at full-time. In the 2002-03 season, Arsenal were in the title race but were derailed by a 2-2 draw at Bolton, followed by a home defeat to Leeds. “I remember Wenger, always very animated in his complaints, on the touchline,” Giannakopoulos says. “These details either motivate you or anger you. For us, it was motivation. Whether it was Mr. Wenger or someone else, it meant we were doing something right, that we were a nuisance, and that we could win games.”

Wednesday’s match will mark the first meeting between the two teams in 12 years, stirring a wave of nostalgia among Bolton fans, remembering the glory days when the club finished seventh and eighth in successive Premier League seasons. Giannakopoulos enjoyed his time in Lancashire so much that he still resides there and often visits the ground now known as the University of Bolton Stadium.

The days of signing players from Real Madrid and Paris Saint-Germain are long gone. Now, Ian Evatt is scouring Newport and Bristol Rovers for talent. After a sluggish start to the season, Saturday’s 5-2 home victory against Reading could be a turning point. Bolton has underperformed since losing the League One playoff final to Oxford United in May, but facing one of the big boys could provide the extra spark needed to continue their journey back to the top.

Arsenal showed against Manchester City that they may have picked up a few tricks from Allardyce’s playbook, but Bolton will once again aim to disrupt the status quo. How can they cause an upset on Wednesday? “Perhaps a motivational speech from Big Sam could do the trick,” Giannakopoulos suggests.