Simpson relishes next bout with Dennis the Menace

The first time Fitzroy Simpson ran into Dennis Wise, the impact threatened the foundations of Maine Road a full decade before the bulldozers began demolishing the stadium officially.

Simpson's career took him from a West Country council house to the World Cup. One of the Reggae Boyz when Jamaica were the smallest country at France '98, he will attempt to reprise the role of giant-killer on Saturday for one of the two smallest clubs left in the FA Cup, Telford United, against a Millwall side whose player-manager he knows of old.

"I hadn't been at Manchester City long when we played Chelsea," Simpson recalls with eyes twinkling. "With 10 minutes gone and the ball nowhere near, Dennis slapped me round the face, laughed and ran off. I left it but I thought: 'I'll get you back later in the game'.

"Eventually, I caught him and it all went off. Big Mick Harford came in and grabbed me. Garry Flitcroft ran over to try to help me out and Mick got hold of him too. I thought he was going to throw both of us over the Kippax Street stand. One paper headlined it 'Fitzicuffs!'"

When the fourth-round draw was made, Telford's players gathered around a television set. After the Nationwide Conference outfit came out at home, they whooped and waited for Manchester United or Arsenal. Millwall, halfway down the First Division, came as an anticlimax. "I was disappointed," admits Simpson. "Then I thought: 'Dennis the Menace'. Nice bloke, tough opponent. I did have a little chuckle to myself."

But then Simpson has always played with a smile as well as a snarl. A Manchester United fan ("Well I do come from Wiltshire," he says self-mockingly), he was discovered by Lou Macari for Swindon. From the former Old Trafford striker, a teetotaller and fitness fetishist, he absorbed pragmatic values that have kept him running well into his 34th year.

Yet he also learned from Macari's polar opposite, Ossie Ardiles, and blossomed further under Glenn Hoddle. "Ossie wanted us to play like Brazil. He'd say: 'If they score three, we'll get four'. When Glenn came in, I thought he was sailing on a cloud; I didn't see his feet touch the floor. I'd always been him in the school playground, so I never quite got over shouting: 'Gaffer, give us the bloomin' ball'."

Simpson soon came under the wing of Peter Reid at Manchester City. "He was player-manager and we also had Steve McMahon. I'd never worn shin pads in training until I went there!"

His "one regret" in football centres on his time in the top flight. "I was 22 and in awe of guys like Niall Quinn, Keith Curle and McMahon, as well as the massive stadium. When I look back I feel I could've given an extra five per cent at City, contributed more and made it last longer."

The latter sentiment certainly applies to his first major FA Cup run, in 1993. "City are two wins from the final, at home to Tottenham, and we go 1-0 up. I'm thinking: 'My God, we're going to Wembley'. Then the wheels fell off and we lost 4-2."

He helped Portsmouth to another quarter-final four years later: home to Chelsea. "The great Terry Venables - Barcelona, England, been there, seen it, done it - was involved with Pompey. Anything he said went and he told us: 'Let Frank Leboeuf have possession because he can't pass'. After five minutes he got the ball. We stood off him as instructed. He hit a 50-yard pass straight to Mark Hughes, who stuck it in the net."

Chelsea won 4-1, one Dennis Wise scoring twice, yet Simpson was already looking to spread his wings. He had once been named in an England Under-21 squad but pulled out injured and was never picked again. Now he and his club-mate Paul Hall wrote to the Jamaican FA to ask about representing their parents' homeland and paid their own way over for a trial.

They joined an Anglo contingent that the home-based players dubbed "UB40" (English reggae band, geddit?) and set about reaching Jamaica's first World Cup finals. "It was like the non-League mentality in the FA Cup," Simpson says. "The United States and Mexico were expected to thrash us, but we had an inner feeling of: 'We ain't gonna let it happen'.

"One day we played in front of 92,000 screaming Mexicans. The next I was on a flight home and the next I played for a Portsmouth XI at Bashley on a bitter night, watched by two men and a dog. Jamaica qualified with a 0-0 draw at home to Mexico. They were never going to beat us - it's a long way from the ground to the airport."

In the finals, he directly opposed Robert Prosinecki in a 3-1 defeat by Croatia and Juan Sebastian Veron against Argentina. "By half-time they were a goal up and we were a man down. Daryl Powell got sent off - I could've killed him! - and everyone's tongues were hanging out. We lost 5-0, but hey, it was a privilege chasing them around."

Jamaica bowed out by beating Japan and Simpson still pinches himself at the memory of an international career that ended after a second, unsuccessful qualifying campaign. Back home, spells with Hearts and Walsall followed before Telford came calling last summer.

With an ambitious chairman, refurbished ground and revamped squad, the Shropshire club looked primed for promotion to the League. A mid-table berth in the Conference suggests they have under-achieved - except in the Cup. In the third round they won 1-0 at Crewe Alexandra, Simpson making Lee Mills' goal. "We scored too early," he laughs. "We had 88 minutes to defend against the best passing team outside the Premiership.

"I never used to like giant-killers. But now that I am one, I'm loving it. I remember there was always an element of fear against the minnows because you're expected to win. That's quite a pressure. Millwall at their best should beat us. If they're a bit below par we've got a chance."

Wise will find him as enthusiastic and spiky as ever. Simpson watched his nine-year-old son, Jake, play for Swindon Under-10s in a 7-1 win over Oxford last week and talks as if he is just starting out himself.

"I'm as passionate about helping Telford beat Millwall as I was when I played for City or Jamaica. It's like our manager [Mick Jones] says: 'Take away the stands and it's still a football pitch'. I still get up in the morning and think: 'I still want to do this. And I still want to win'."