The one-time footballer was shattered when a projected £3m move from Sheffield United to the Ibrox club fell through. "I came to Scotland and went to the last game of the season," he recalled. "The chairman sorted out the deal - a five- year contract - but, by the time I got back to Sheffield, it had evaporated. I was absolutely devastated.
"Dick Advocaat was in charge then and Rangers had a great team. It would have been fantastic to have been involved in European nights and things like that. I look back now and think 'what if?' Unfortunately for me, it fell through at the final hurdle. I still don't know why, as everything was agreed from my end. I believe agents were being greedy; it's just one of those regrets in life.
"When I went there [to Ibrox], the atmosphere was unbelievable. That's one of the things that brought me to Scotland when a lot of people were advising me not to come. I just wanted to be a part of that atmosphere."
Woodhouse eventually lost his passion for football and turned to boxing in 2006 because "I loved fighting and, instead of getting locked up, [I decided] I'd try and earn a living out of it".
He promised his dying father, Bernard, he would win the British title and achieved that target in February. Now he is putting it on the line in a light-welterweight unification bout with Limond, the Commonwealth champion.
Woodhouse said: "He [his father] died of a stroke and, when I went to the hospital to see him, I said [to him] on his deathbed that I'd win the British title for him. That's why [doing so on] February 22 meant so much to me: because, once I made that promise, I was determined to keep it, no matter what.
"I was relieved because it had been plaguing me for so long. I thought I'd never achieve it and it would be hanging over me the rest of my life. People are saying it's the best they've seen me box. They don't understand the pressure [on him] was unbelievable; I knew I had to win. Now you'll see the very best of me because I'm going there [to Glasgow] to enjoy myself.
"[The fight on] February 22 will be the one I'll never forget but [the one against Limond on] June 27 will be the biggest night of my life. I made it clear very early on that the fight I wanted was [against] Limond. There are two belts in Britain so I want to unify them and be No.1.
"Scotland was one of the few places that really excited me because of the atmosphere. I've watched [fights involving] Ricky Burns on TV and the hairs on the back of my neck were standing up.
"It's going to be spine-tingling being involved but unfortunately they [most of the spectators] are not going to be cheering for me. I'm just going to enjoy it; whether they're with me or against me, the important thing is I can feed off that atmosphere.
"People asked if going to Glasgow was wise but there's not one fighter who has a bad word to say about it [having done so]. I don't want any favours, just a good crack of the whip. The Scottish people are fair and they'll like my style. I understand they'll be behind Willie but, by the end of the night, I hope I [will] have gained their respect."
Woodhouse, 34, and Limond, 35, are at entirely different stages in their careers. The British champion believes a special fight is in the offing because both men have no other options. "The bottom line is neither of us can afford to lose," he said. "You've got to give us respect for taking this [fight] because everything is on the line. Neither of us has got anywhere else to go, so you will have two desperate fighters in there. You've got two men who are willing to do absolutely anything and that usually makes for a hell of a fight.
"We're at completely different stages of our careers. Willie made his debut in 1999 when I was playing for Sheffield United. If someone had told me I'd have been fighting him for the British and Commonwealth titles then I'd probably have locked them up. It just shows you how life can turn out.
"I'm under no illusions that this is probably going to be my hardest fight. Only the best of the best have beaten him. If you're not the real deal, you don't get past Willie Limond. I'm someone who rises to the occasion: the bigger it is the better I perform. I'm looking forward to coming to Glasgow and giving fans a night they won't forget."