27/11/08 - UEFA Cup - Portsmouth 2-2 AC Milan
Following their FA Cup triumph, Portsmouth embarked on a European journey. In November 2008, the renowned Italian powerhouse AC Milan visited Fratton Park to face Tony Adams' Portsmouth. Despite being perceived as underdogs against the seasoned and decorated Milan side, Portsmouth not only held their ground but came tantalizingly close to securing a surprising victory over Carlo Ancelotti's team.
All the action unfolded in the second half, with Portsmouth seizing the lead in the 62nd minute through a Younès Kaboul header. The south coast team's fortunes soared further when Nwankwo Kanu, a former Arsenal striker and FA Cup hero, netted a goal in the 73rd minute to double Portsmouth's advantage.
Despite Portsmouth's valiant attempts to safeguard their lead with just 17 minutes remaining, AC Milan's superior quality eventually manifested on the Fratton Park pitch. Goals from the Brazilian maestro Ronaldinho and the prolific Filippo Inzaghi, the latter finding the net two minutes into injury time, shattered Portsmouth's hopes as the match concluded in a captivating and hard-fought draw.