The pain of watching underwhelming former England forward Darius Vassell score the winner in that particular 2007 FA Cup tie was only outmuscled by the vice-twisting pain in my right ear watching the match in my uncle Len's living room.
A quick glance back at the highlights does little to make the memories happier. A relatively strong Owls side who have not been surpassed in terms of league position by following squads in the intervening seven years attempted valiantly to stave off Stuart Pearce's Manchester City with a team consisting of Joey Barton and Steven Ireland alongside the hapless Vassell.
But if the years between the two ties have been defined by success (City's clutch of trophies, star players and two league titles) and lack of it (the Owls endured another stint in League One since), then tonight's match can be seen as immaterial.
The Blue and White Wizards entered the game in fine form, with defensive fortitude ironically proving the bedrock of a side who have calmly and rightfully taken up sixth position in the league unexpectedly this season.
Whilst few of the #WAWAW ('We're all Wednesday aren't we?') chanting faithful harbour serious confidence a promotion push is possible despite the Owls' lofty position, there's still plenty of the emotion carried in the name of Everton loanee Hallam Hope. Even a failed takeover by Azerbaijani businessman Hafiz Mammadov, which collapsed after a long summer earlier this month, has failed to dampen spirits around S6.
But tonight's game proved that dreams of promotion need to be tempered. The realities of the modern game mean that, without investment, the Owls cannot expect to compete with a team that were so long their counterparts in near-achievement. Not least as boss Stuart Gray fielded a weakened team against their big money opponents.
Wednesday proved resolute and confident at times in the first half against the holders. A defensive line up led by lone striker Gary Madine valiantly fought off a Sky Blues team featuring several players who appeared in this summer's World Cup including Edin Dzeko and Frank Lampard.
And it was Lampard, fresh from bashfully sticking a knife into Chelsea hearts at the weekend, who clipped the Owls' wings, slotting home from James Milner's cross just after half time.
There was, predictably, only one winner after the Romford boy's finish as Man City showed their class. Kamil Zayatte's sending off aided the inevitable and Lampard's rounding off of the victory summed up a night which said a lot about the last 15 years for Wednesday.
The margin of the eventual victory may have punctured the Hillsborough team, who have undoubtedly been looking forward to this glamour tie, but it's irrelevance must be noted. Wednesday's league position both now and at the end if the season will dictate whether a buyer - and thus a future - can be carved out for the much-patronised 'sleeping giant'.
A flashy win against globally recognised opponents fielding a strong side would have been nice, but not essential in attracting the kind of overseas investors we need. Chairman Milan Mandarić this week claimed he turned down a multi-million offer for an Owls player in the transfer window, but he needs to stick or twist in deciding whether to invest in the Owls or ship out quickly. Could this be the decisive season in Wednesday's rudderless recent past?
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