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- Sweater
- Year: 1998-1999
- Player: Ariel Ortega, Zoran Jovičić, Emanuele Pesaresi
- Size: L (63 cm x 68.5 cm)
- Brand: Asics
- Sponsor: Deawoo
- Details: Very good condition apart from some slight pealing on the Daewoo sponsor.
In the 1998-1999 season, Sampdoria, featuring a revamped squad, participated in the Intertoto Cup but was eliminated by Bologna in the fourth round. The team started the league campaign fairly well, but an injury to star striker Vincenzo Montella sidelined him for most of the season. Without his goals, the team struggled and faced challenges, resulting in early exits from the Coppa Italia (once again at the hands of Bologna) and a position near the bottom of the standings. In mid-December, following a 5-2 defeat to Lazio, Luciano Spalletti was dismissed, and David Platt took over as manager, joined by Giorgio Veneri on the bench despite lacking a coaching license. In their first match together, Sampdoria managed a 2-2 draw against AC Milan, but this positive result quickly faded as the team garnered only three points from the next six matches. After a 2-0 loss to Perugia, Platt resigned despite the club's support. Luciano Spalletti was reinstated, but even with the return of Vincenzo Montella and 21 points collected in the last 15 days, the team could not avoid relegation. Their struggle was compounded by an inability to secure points away from home, with just one win and a total of seven points throughout the season. The relegation was sealed on May 16 during a 2-2 draw with Bologna, where the equalizing goal came in the 94th minute from a controversial penalty awarded by referee Alfredo Trentalange, who later acknowledged his mistake. In the Coppa Italia, Sampdoria advanced past Verona in the round of 16 but was eliminated in the quarter-finals by Bologna, again due to a last-minute penalty.