Woodhall hung up his gloves after losing a WBO world title fight when the Welshman was in his ascendancy nearly 16 years ago,
The two super middleweights were friends before the fight and still bear no grudges towards each other, despite the leather swapped before Calzaghe stopped him in the 10th round.
On Thursday night, Woodhall will be reunited with his nemesis when he interviews him during a show at Bar Sport's Premier Suite in Cannock.
Calzaghe will take centre stage at Scott Murray's venue across the West Midlands, where Woodhall regularly asks the questions of the after-dinner speakers.
He said: "It will be great, I know Joe really respects me because, everytime I see him, we throw our arms around one another!
"I've heard him tell people how he thinks I was a great fighter and for that compliment to come from him is a real feather in my cap.
"When you hear that from him, who has beaten the very best in the world, I've not done too bad as a kid from Woodside!"
Woodhall is a former WBC champion and had lost his crown on points to Markus Beyer a year earlier when the Calzaghe fight came up.
It was considered the final opportunity for the 32-year-old to restore former glories, with Calzaghe six defences into a record-breaking tear as WBO boss.
Frank Warren made the fight, with that honour on the line, for a bill that took place on 16 December 2000 at the Sheffield Arena.
Woodhall recalled: "It was a weird situation, before we fought we were good friends but we had to box each other, because we were managed by the same promoter.
"We had to show our professionalism, put that to one side and get on with it. The fight was offered to us and neither one was going to back down.
"It just had that little bit of extra spice to it and everyone wanted to see it happen. It was a very good British world title fight."
The two touched gloves and went to work, with pleasantries going out of the window when Calzaghe countered to land a right hand flush in the opening minute.
Woodhall regrouped to up the pace and land the better punches in the second, with his best work coming in the earlier rounds.
By the second half of the fight, Calzaghe had started to take control and he went up the gears towards the finish.
A right hand over the top as both fighters traded bowled Woodhall over in the dying seconds of the ninth but, despite being bloodied, he saw the bell.
Calzaghe resumed his onslaught when action resumed in the 10th, pinning Woodhall onto the ropes and letting his punches go.
Woodhall covered up and took the blows until referee Roy Francis stepped in to spare him further punishment, 28 seconds into the session. He still has "no complaints."
The fighters embraced as did their corners, with both combatants trained by their father. Enzo Calzaghe and the late Len Woodhall were also well-acquainted.
He said: "I wasn't a knockout expert, I used what I'd got and I listened to my old man. I was tall and rangy and very fit, because I trained really hard. My dad and Enzo were good friends, too.
"I think it was always close and competitive, I think I had some good rounds in the contest and I had some moments where I think I did OK.
"I came forward and hit him with some really good shots that just bounced off him and, in the end, he came through it.
"As an opponent, Joe just had all of the answers for me. He's an under-estimated fighter technically, too. He was exceptional.
"He had a great chin, he was powerful, he could fight on the inside or at range and he put me up against it. He was that little bit too sharp for me.
"You only know that when you are in there with him, but it still took him 10 rounds to stop me. He was a good 12-round fighter, he finishes as strong as he starts."
It was one of only two TKO defeats that befell Woodhall in the paid ranks, the other for the WBC crown at middleweight in the 12th and last round against the world-class Keith Holmes in 1996.
His earlier pro career had produced Commonwealth and European middleweight titles and he called time with 26 wins from 29 bouts, with 16 victories inside the distance.
He'd previously boxed as an amateur to the tune of a gold medal at the Commonwealth Games and bronze at the Olympics.
He would settle for bronze at the 1988 Seoul Games, where he was defeated over-the-distance by future pound-for-pound great Roy Jones Jnr.
Calzaghe's last fight came against Jones Jnr in November 2008, his 46th and final win without reply coming on points as he retired undefeated at the turn of the following year.
Woodhall said: "In a nutshell, Calzaghe is the best pro I fought. Roy Jones Jnr was my toughest amateur test and he was the hardest after I turned over.
"I went to the Olympics and was beaten by the best boxer in the tournament, who didn't have it all his own way. I won the second round of the three, remember.
"I'd been a world champion, so it was a good win for Joe and he got a lot of credit for it. I was a genuine contender.
"It was my last chance to win a world title again and become a two-time champion and I already considered him, at the time, to be the best super middleweight out there.
"I wanted to test myself and, if you're a true fighter, you go after the top names, but I was coming to the end of my career anyway.
"When you've had enough mentally, that's probably a bigger question on your career than the physical side of it. That's when you know it's time to call it a day.
"Once he'd beat me, I'd had enough. There's no turning back after that, you can try and have a go again but, deep down, you know it's over. I was clever enough to see that clearly."
It will be a family affair for Calzaghe at Bar Sport with Enzo and his uncle Sergio joining him for the event.
The family story has just been recounted with the documentary 'Mr Calzaghe,' a feature film that was released last year.
Tickets for the night with Woodhall and Calzaghe are still available, starting from £60. The 'platinum' option includes a seat and four-course meal.
A 'silver' pass is £95, with the same benefits plus a professional photograph with Calzaghe. 'Gold,' at £150, also allows entry to a private meet and greet room beforehand.
There are options for 'bronze' ticket holders, most of whom have already purchased, to pay an added fee of £35 for a photo.
For more information and to book places for the show, get in touch with Bar Sport directly by calling 01543 572 092.