AT 10.35pm on Wednesday, in formation with three bodyguards, Roman Abramovich strolled across the Stamford Bridge turf. He paused to read a text message before glancing up, his gaze lingering on the deserted seats of the Shed End, its blank jumbo screen and the empty goal into which Andres Iniesta had scored. Abramovich walked on. What did he think when he paused? On that, everything, for a football club, depends. Because only an hour after Iniesta had wrecked blue hearts, Chelsea had their most important player on the pitch.

Like a masochist with a tool box and a gift for lateral thinking, Chelsea keep coming up with strange new ways to torture themselves in the Champions League. Wednesday was every bit as wince-inducing as the penalty shootout in last year’s final and worse than the agonies of Anfield in 2005 and 2007.

But a logician might look at recent torments coldly. Chelsea have had, more or less, the same first-choice line-up for three seasons. It was not good enough to win the Champions League or Premier League in 2006-07 or 2007-08 and 2008-09 has turned out the same. Where is the shock, the sudden pain? What did Chelsea expect? The club have stood still while Manchester United, Liverpool and, in Europe, Barcelona have moved on. Sir Alex Ferguson says progress is a bus that, if you don’t board it, will leave without you.

Chelsea’s stasis has been down to bad choices involving managers; sacking Jose Mourinho, appointing Avram Grant, deciding Luiz Felipe Scolari was right for English football. But it has also stemmed from Abramovich’s paralysis. The vanity purchase of Andriy Shevchenko was his last big splurge. Shevchenko cost £30m in 2006 during a summer when Salomon Kalou, John Mikel Obi, Khalid Boulahrouz and Ashley Cole were recruited in deals worth £50m.

In five subsequent transfer windows Chelsea’s net spend has been less than West Brom’s: £5m. Their squad now has just 20 regularly involved players, eight of whom are in their 30s. Like a white elephant — only slower — Shevchenko will be back to compound things next month when a failed loan spell at AC Milan comes to an end.

Thinking of Chelsea as impoverished takes some getting used to but Abramovich’s property is beginning to resemble one of the palaces of the Tsars, full of old, expensive items (Michael Ballack, 33 in September, is to be granted a one-year contract extension) but declining in relevance to a changing world. Abramovich, who is said to like playing cards, faces the classic gambler’s choice of whether to stick or twist. He is still super-wealthy, worth £7 billion according to the 2009 Sunday Times Rich List, but his fortune has declined by 40% in 12 months and nobody can be comfortable losing almost half their money, no matter how much they have.

His choice with Chelsea is whether to dust himself down after his latest disappointment and go again, reopen his wallet and throw further roubles at their troubles. Or does he shrug and conclude the club still have enough footballers (which they do) to provide, if not national or European champions, certainly a pleasant enough diversion on the 50-odd days a year tax issues let him spend in the UK?

In January 2007, in a briefing after they bought Liverpool, Tom Hicks and George Gillett claimed to have seen a leaked document detailing Abramovich’s plans for Chelsea. What appeared wild spending had actually been a carefully costed five-year investment plan. Back in 2003, when he was looking to own one of the world’s top clubs, football business analysts told Abramovich the price would be £500m for a ready-made entity, such as Arsenal, or less for an up-and-coming team, with the surplus cash going into transfers, which is what he chose, buying Chelsea for £140m and sinking £220m into player recruitment over his first three seasons.

Including wages and improvements to the club’s infrastructure, Abramovich’s total net spend on Chelsea reached £578m in February 2008. Hicks and Gillett, who predicted spending would stop once Abramovich’s personal outlay went significantly over £500m, were eerily accurate.

Supporters must hope their sugar daddy feels the injustice of Wednesday as keenly as they do and resolves to come back next season with a side so powerful no amount of refereeing malfunctions could prevent them winning the Champions League.

Chelsea chairman Bruce Buck, Abramovich’s confidant, emitted mixed signals at a fans’ forum a few days before the first leg against Barcelona. Buck predicted a turnover of players in the summer with “three, four or five” leaving and “several” arriving but added: “In the large part we would like to fund acquisitions with sales.”

However, he tantalised the faithful by suggesting Abramovich was ready to sanction one mega-signing, perhaps a new talisman to invigorate the squad. “If the player came along at the right price, and it was a hefty price, and it worked for Chelsea then Abramovich would be willing to invest more money,” said Buck.