first round in Nijmegen, Netherlands on March 19, 1995. As a rising star of Swiss kickboxing, Maksutaj was invited to fight at Japan's K-1 Fight Night, the first-ever event held by the K-1 promotion outside Japan, on June 10, 1995, in Zurich, Switzerland. There he lost to Surinamese veteran Orlando Wiet via a second-round KO. Returning to K-1 a year later at K-1 Fight Night II on June 2, 1996, he gave a "Fight of the Night" performance in a losing effort against Seido karate stylist Taiei Kin. He was knocked down in round two and lost by a unanimous decision after a five-round war. Despite failing to earn a victory on kickboxing's biggest stage, he continued to improve and ended that year's campaign with a knockout of Faizal Reding on November 2, 1996, in Zurich, to take the International Sport Karate Association World Super Middleweight () strap. Dominance at light heavyweight and cruiserweight (1998–2000) He made the first defence of his ISKA world title against Moussa Sissoko, stopping the Frenchman inside three rounds in Winterthur on November 7, 1998. Following this, Maksutaj began to move up in weight to the light heavyweight class and established himself as one of the division's elite by making a successful return to K-1 and then winning three world titles in the space of five months in 1999. After his comeback to K-1 on June 5, 1999, at K-1 Fight Night '99, where he earned his first victory in the promotion by flooring Winston Walker three times in the third round en route to a technical knockout win, he headed to Pula, Croatia a month later to challenge double world champion Igor Ivošević. He was able to knock his opponent out in round four and came away with both the World Association of Kickboxing Organizations' Pro World Light Heavyweight () and the WKA World Super Light Heavyweight () belts. Maksutaj then closed the year out with a fifth world championship win, outpointing his Surinamese opponent Ashwin Balrak for the World Professional Kickboxing League (WPKL) World Light Heavyweight (-) title in Sarajevo, Bosnia and Herzegovina on December 11, 1999. In 2000, Maksutaj moved briefly back down to super middleweight to successfully challenge for the WKA World Super Middleweight (-) Championship, winning on points over Ivica Sukošić in Pristina in his birth country of Kosovo. He would then return to light heavyweight and KO Aurélien Duarte