"Sex and death", Woody Allen once remarked. "Two things that happen once in a lifetime – though at least after death you're not nauseous". To this short list he might have added "…and Luton Town Football Club winning a major trophy, or any trophy for that matter". Silverware on the Kenilworth Road mantlepiece is about as commonplace as a dreidl in the Vatican, and 24 April 1988 was the day, the one and only day, we called in the engravers.

Luton then were as West Brom are today, up and down more often than Benjamin Netanyahu's Y-fronts, our flirtation with the top division never quite blossoming into a full-blown affair. But in cup competitions we shone, as the mighty Arsenal were to find out that sunny Sunday afternoon as both teams took to Wembley's old meadows for the League Cup Final, or whatever the sponsors called it back then.

That I elected in the first place to lend my vocal support to the decaying rubble we Lutonians call a stadium (all regulations governing health and safety mysteriously stop at the ground's turnstiles, both of them) showed early and unsettling signs of perversity, and perhaps gave a clue to the years of therapy that were to follow.

The fact is I wanted to be different, and let's face it, when you're a Jewish kid growing up in Hendon Central, fairly drowning in a tidal wave of Spurs and Arsenal fans, Luton is about as different as you can get. Today I can pass it off as some sort of post-modern ironic statement. Back then it was just plain weird.

Or was it? For Luton – and tell me if this is not perversity itself in a town where Vauxhall looms larger than God - is probably the most Jewish club of the lot, the Red Sea of Kenilworth Road parting at various times to engulf a Jewish chairman, Jewish manager, and that most exotic of species, a British-born Jewish player – respectively David Kohler, David Pleat, and the much travelled and largely forgotten Barry Silkman, journeyman ball-juggler who graced our midfield for a few brief games between spells at some dozen or more other clubs where the catering was doubtless better, from Maine Road to Maccabi Tel Aviv via Orient and Palace and Hereford and…oh, the list goes on and on and on…

Silkman was a contemporary of Kevin Keegan with, arguably, less natural ability than the whingeing Geordie, but an infinitely better perm, while Kohler's main claim to fame, apart from the ability to win any number of Rodney Bewes lookalike competitions, was his obsession with what he modestly called his Kohlerdome, an all-singing, all-dancing, all-purpose arena replete with moveable pitch and retractable roof, at a cost that could fund Joey Barton's legal bills for next decade-and-a-half.

The stadium never happened. Nothing under Kohler happened, save for the wholesale disposal of our better players, the signing of no-one that actually involved the handing over what you and I know as money, and the inevitable and horribly rapid descent to the basement of the Football League.

And when finally Kohler was consigned to the footballing catacombs by fans bearing letter-bombs, his legacy was a team in which my late grandmother, aided only by her frame and a few puffs of Ventolin, would comfortably have held her own.

All of which leaves me hankering for the class of '88, the team of nine internationals, fashioned by Pleat, inherited by Ray Harford, and managed once again by the crumple-faced cliché-meister whose manic jig on defeating Manchester City with the last kick of the 1982/83 season to preserve our top flight status was one of the defining moments of the 20th century.

Armstrong set foot on the Moon, Mandella walked free from Robben Island, and Pleat ran around like an idiot. The Earth may not have moved when Pleatie weaved his spell, but there were tremors in Bedfordshire from Sandy all the way to Leighton Buzzard, street parties the likes of which Flitwick had never before seen.

And yes, you read me right – nine international players, including the progeny of a South African ANC activist (Brian Stein) and a Nigerian military attache's son (Emeka Nwajiobi). Unfashionable we may be. We could sign Beckham, Zidane and Ronaldinho, bedeck the entire squad in Armani shirts and Paul Smith jocks, and change our name to Real Luton, and we'd still be about as chic as Roger Whittaker.

But we were fielding players called Pasquale Fuccillo, Bontcho Guenchev, and Herve Bacque long before Greater Europe started beating a path to the Premiership door. Goodness me, but the word galacticos was first uttered not in Madrid's Bernebau Stadium, but about 50 metres north of the Dallow Road Industrial Estate.

We beat Arsenal 3-2 that day. God, we were so much better it was embarrassing, and never mind a Luton crossbar more pockmarked than a Sarajevo apartment block. Spurred on by Andy Dibble's 85th minute penalty save from the ever-hapless Nigel Winterburn, we staged the finale of which legends are made. Arsenal hadn't read the script. We were fated to score twice in the last five minutes, retribution for always losing to them in the league. This was Pulp Fiction, we were Samuel L. Jackson, and did we ever strike Arsenal down with a vengeance.

Fate these days finds Luton's jigsaw box assemblage of schoolboys and loan-players, has-beens and never-will-be's, tripping the light fantastic to Colchester, Southend and other footballing outposts where the leading scorer is rivalled by the tea lady in terms of earning power.

Our local derby, now we've lost Watford to a higher calling, rests on drawing Milton Keynes Dons in the Cup, our one trip abroad is against Cardiff City, our hopes of a new stadium got lost more than a decade ago in some kind of bureaucratic Bermuda Triangle, and the one policeman that patrols outside the ground does so for the sole purpose of throwing people in.

Things do not look good. The town – once derided byThe Idler magazine as "the crappiest town in Britain" – still struggles to grasp the twin concepts of sanitation and pavements, while the team's fortunes, relatively sound just now at midway in the Championship, will surely once again nosedive once the big bad wolves of the CWM brigade (that's Clubs With Money) come a-huffing and a-puffing, cheque books in hand, for our better players, whom doubtless we'll let go for petty cash just as we've always done and continue to do simply to survive. And our manager will doubtless be dismissed, like Joe Kinnear, by text message just as he gets the team looking like viable contenders i.e. now.

Such is the plight of the smaller club. We can spot a good player, but we can't keep him. We can top the table, but we can't stay there. We can only go so far before it all ends in tears. But Luton are my team, handed down by God on Mount Sinai, and they'll be my team until death, or a spectacularly lucrative takeover bid, do us part.