There was a buzz on the south coast of England as a Premier League underdog playing in Europe for the first time prepared to welcome the mighty AC Milan.
On a night that was already a pinch-me moment for the home fans, excitement turned to disbelief as their side went 2-0 up against the seven-time European champions - only for the Italian giants to burst the bubble with two late goals in a 2-2 draw.
Because that Milan team that faced Portsmouth 18 years ago was very different to the one that lost 3-0 to Bournemouth in the Europa League last week. In fact, those two trips to the south coast serve as a barometer of the decline of the Rossoneri.
Why AC Milan have lost their aura
Looking back now, it is incredible to see how many superstars graced the Fratton Park turf during that UEFA Cup tie in November 2008.
Dida, Gennaro Gattuso, Kaka, Filippo Inzaghi and Andriy Shevchenko all started the game, with Clarence Seedorf, Ronaldinho and Alexandre Pato coming off the bench. Ronaldinho scored a brilliant free-kick to halve the deficit, before Inzaghi snaffled an equaliser in stoppage time. Oh, and Carlo Ancelotti was their manager.
Milan had reached three of the previous six Champions League finals, and eight across the previous two decades. When it came to European royalty, they were on a par with anyone.
While the visit of the Serie A giants would have created a similar buzz in Bournemouth as it did in Portsmouth 18 years earlier, the side that played at the Vitality Stadium was a pale imitation of the one that lined up at Fratton Park.
Whereas the team that drew with Pompey was full of superstars, the only genuinely world-class player in Milan's squad last Thursday was Luka Modric, an unused substitute who turned 41 in September. The starting line-up included English trio Fikayo Tomori, Ruben Loftus-Cheek and Omari Hutchinson, who all left the Premier League - two permanently and the latter on loan from Nottingham Forest - in search of more game-time.
The truth is that Milan cannot attract world-class players at their peak anymore. They haven’t been a force in Europe for nearly two decades, reaching the Champions League quarter-finals just twice since they last lifted the trophy in 2007.
The iconic badge and red-and-black shirt are their only link with the great Milan teams of yesteryear. Even the San Siro, one of world football's most prestigious stadiums, will soon be demolished, severing another connection with the past.
European football is poorer for it, because for many years Milan had an aura that few clubs could match.
This is the club of Arrigo Sacchi, the 4-0 demolition of Barcelona in the 1994 Champions League final, George Weah’s solo goal against Verona, the imperious defensive partnership of Paolo Maldini and Franco Baresi (and the long-standing myth about their goals-against record), plus many more iconic moments, matches and individuals.
This is the club who were front and centre of Serie A in its 1990s heyday, when millions of British football fans fell in love with the league through the cult TV show Football Italia.
So, what went wrong? As with many things, the answer comes down to money.
Two days before Ancelotti’s side faced Portsmouth in 2008, Bournemouth drew 0-0 at home to Morecambe in League Two in front of 3,068 fans. The Cherries began that season on -17 points and at one point were reportedly five minutes from liquidation, before eventually escaping relegation under Eddie Howe.
It is in that context that Bournemouth beating Milan is a fairy-tale, but only in that context. Because when you compare the two clubs in 2026, there is no reason why the Cherries should not beat Milan.
The Rossoneri are flying high in Serie A while Bournemouth are in the bottom half of the Premier League, but that is largely irrelevant due to the financial muscle of the English top flight, which boasts a domestic TV rights deal that dwarfs its rivals.
According to Transfermarkt, the market value of Bournemouth’s squad is €624m (roughly £522m), whereas Milan’s is €503.2m (£421m). The Rossoneri have the fourth-most valuable squad in Serie A but would be 14th in the Premier League, three places below the Cherries.
The financial advantage is laid bare in the 2026 Deloitte Football Money League, which ranks the highest revenue-generating clubs in the world. Milan placed 15th with an annual revenue of €410.4m (£344m), below seven Premier League clubs - the ‘Big Six’ of Liverpool, Manchester City, Arsenal, Manchester United, Tottenham Hotspur and Chelsea, as well as Aston Villa.
Bournemouth were 26th with a revenue of €218.5m (£183m), but the fact they were only the 13th-highest Premier League club shows the financial power of the English top flight. In terms of Serie A teams, only Inter Milan (11th), the Rossoneri and Juventus (16th) placed higher than the Cherries.
The top four sides in the Money League were Real Madrid, Barcelona, Bayern Munich and Paris Saint-Germain, followed by the Premier League’s ‘Big Six’. This encapsulates the balance of power in European football: you have those four superclubs, then the Premier League, then everyone else.
The Champions League is a case in point, with Real, Barca, Bayern and PSG sharing 12 of the past 16 titles and ‘Big Six’ clubs winning the other four. In the past two seasons, Premier League sides have won both the Europa League and Conference League, too.
That is why Milan’s defeat by Bournemouth should not have shocked anyone. Some will see it as a positive that historically ‘small’ clubs like the Cherries can beat giants like Milan, but in reality this only applies to Premier League teams. Barring the odd exception, a club of Bournemouth’s size in any other league would not be able to assemble the same quality of squad.
One of those exceptions is Como, who were on the other side of an Anglo-Italian giant-killing when they thumped Manchester United 4-1 in the Champions League 24 hours earlier. United are a mess, but they have the financial clout to become a force once again. You cannot confidently say the same about Milan.
The Rossoneri are not the only multiple European champions who are a shadow of their former selves - just ask Ajax, Benfica and Juventus. However, the financial landscape has changed so much that there may be no way back.
