AC Milan head to Bournemouth on Thursday in the Europa League, 18 years on from their last visit to the South Coast.
Carlo Ancelotti’s side travelled to Portsmouth in November 2008 to face off against Pompey in a UEFA Cup clash.
Portsmouth were massive underdogs with a team full of dependable but not flashy Premier League journeymen. David James, Younes Kaboul, Sylvain Distin, Papa Bouba Diop, Peter Crouch and Kanu all started.
Even though they boasted a star-studded line-up that included Gennaro Gattuso, Kaká, Filippo Inzaghi and Andrey Shevchenko, Milan shockingly fell behind at Fratton Park.
Managed by Tony Adams, Pompey kept the tie scoreless until half-time. Following the interval, they amazingly scored twice to stun the Rossoneri.
Firstly, Kaboul got on the end of Glenn Johnson’s cross to head past Dida in front of a raucous Fratton End.
Soon after, Kanu doubled the hosts’ advantage when he finished from close range.
Ancelotti had just assembled his Avengers to rescue the tie when Kanu scored, sending Clarence Seedorf, Alexandre Pato and Ronaldinho on in between Portsmouth’s first and second strike.
Ultimately, Milan were able to claw back a draw. Ronaldinho curled a free-kick past David James before Inzaghi broke Pompey hearts by poking home in stoppage time.
Yet, the tie is still remembered as a famous night at Fratton Park with Ronaldinho labelling it as one of the ‘best atmospheres’ he played in.
Bournemouth will be hoping to go one better than their South Coast rivals on Thursday by getting the win, but Ruben Amorim’s team will prove a stern test after a fine start to the season.