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- Home Jersey
- Year: 1999-2000
- Player: Dennis Bergkamp, Thierry Henry, Patrick Viera
- Size: XL (59.5 cm x 72 cm)
- Brand: Nike
- Sponsor: Sega
- Details: Excellent condition, home shirt with classic Dreamcast sponsor. Baggy design.
Arsenal Football Club's 1999–2000 season marked their eighth in the Premier League and their 74th consecutive in England's top flight. The team concluded the campaign in second place, trailing Manchester United by 18 points. Arsenal faced disappointing exits in both domestic cup competitions, losing to Leicester City in the FA Cup fourth round replay and to Middlesbrough in the Football League Cup. Their European journey saw them exit the UEFA Champions League group stage for the second successive season, but they secured a UEFA Cup spot with a third-place finish. Arsenal progressed to the UEFA Cup final against Galatasaray in Copenhagen, where the match was marred by fan clashes. After a goalless draw, Arsenal lost 4–1 on penalties. During the summer transfer window, Arsenal made significant signings including defenders Sylvinho and Oleh Luzhnyi, and striker Thierry Henry, who arrived from Juventus for a club record fee. The departure of Davor Šuker to Real Madrid followed Nicolas Anelka's move in the opposite direction. Meanwhile, Steve Bould moved to Sunderland and Stephen Hughes joined Everton later in the season. Arsenal's inconsistent league performances, especially away from home, prevented them from seriously challenging Manchester United for the title. Midfielder Patrick Vieira faced a suspension in late autumn after a confrontation with Neil Ruddock of West Ham United. Notably, Arsenal staged a memorable comeback against Chelsea in October, with Nwankwo Kanu scoring a hat-trick in the final 15 minutes. A strong run of eight consecutive wins from March to May lifted Arsenal from fifth to second place, ending the season with 73 points.