Ronnie Henry: Tale of the two Ronnies shows that it really is a funny old game

It has taken some time but Ronnie Henry will finally take the field for a Tottenham Hotspur first-team match on Sunday. That he will be in the opposition line-up does not spoil the story; rather, in a sense, it completes it.

Henry, born into Spurs royalty as the grandson of Double-winning full-back Ron Henry, suffered rejection by his boyhood club after getting no nearer a senior outing than a place on the bench for a Premier League game at Old Trafford as an 18-year-old in 2002.

Told by David Pleat to find a new club, he had spells at Luton Town and Dublin City which ultimately came to naught – the former were in administration, the latter "went bust" – but eventually Stevenage provided a second chance and here he is, seven years and "close to 350 games" later, preparing to face his old side in the FA Cup fifth round.

"It feels like a big circle come back round, playing them again," says the 28-year-old. "When I was sitting watching the draw I couldn't believe it when Tottenham came out – for me and for my family it is a dream come true."

A right-back, Henry operates on the opposite flank from his grandfather, who made 287 appearances for Spurs, and won not just the 1961 Double but also a second FA Cup and the European Cup Winners' Cup. "I've watched a few of the clips. He used to put them on for me," says Henry, who cites his grandfather, now 77 and suffering from Alzheimer's, as an enduring inspiration. "He has been there and done it and I want to do what he has done, if not more. I am having a good crack at it."

If the heights Ron Henry reached seem Himalayan compared with life at the Lamex Stadium, it is worth noting the climb his grandson has already made just to step out against Harry Redknapp's team. "Once Glenn Hoddle left as Tottenham manager, things didn't work out for me. It was tough to take. All my family are Spurs and I was there for a long time. I found it hard to claw my way back up."

Stevenage offered a route to redemption that went way beyond becoming the first cup-lifting captain at the new Wembley after winning the 2007 FA Trophy. "Graham Westley gave me the chance to come to Stevenage, I know it's dropping a long way but I haven't looked back since, getting promoted from the Conference [2010] and League Two [2011], and you never know, we might be promoted from League One into the Championship."

Westley, who left for Preston last month, was a huge influence. His methods may not have made Stevenage popular – accusations of gamesmanship followed their progress – but his full-day training got the best out of his players. "They were long days, so we know each other inside out and as a group of lads we stick together."

Westley's successor Gary Smith, a former Arsenal scout, has won his first two matches – beating Notts County in the FA Cup fourth round, then Sheffield Wednesday at Hillsborough on Tuesday. "We hadn't played for over two weeks [because of frozen pitches] and hadn't actually trained on grass so it has been difficult on top of actually losing our manager, which was a bit of a blow to the club and the players because we've been with him a long time. But the new gaffer has got onside of us and seems a really good manager."

But can sixth in League One really upset third in the Premier League? "Last year we played Newcastle in the FA Cup at home and we beat them, so the lads are going to believe. We have come through some tough rounds already – we've beaten Reading away. Anything can happen with Spurs coming to the Lamex."

As with Chris Day, Stevenage's former Tottenham goalkeeper and another lifelong fan, the visitors will hold no surprises for Henry. "I try and go to as many games as I can at White Hart Lane and they play great football," he says. "Playing them, I need to show – and the other players too – how far we've come and see if we can cope with top players."

That might be easier said than done with Gareth Bale bolting down his flank. "Hope he has an off day" is the plan for stopping the Welshman, he jokes, but no matter what unfolds it will be a day to remember in the Henry household. "My wife and two kids will be there. My five-year-old son, Louie, told me the other day he is going to wear his Stevenage shirt with a Tottenham badge on it. I said to him, 'At least one of your teams will win'."