The two managers will do battle at the Riverside stadium that Monk called home for six months before his controversial sacking, which arrived just hours after a 2-1 win over Wednesday at Hillsborough in December 2017.
Former England international Woodgate was involved in the club’s youth set-up during that tenure and in the lead-up to tomorrow’s clash admitted Monk was a little distant during his time there.
But the Wednesday boss, now 40, has made clear his support for his latest successor, who was promoted to the Teesside top job in the summer. Boro lie 15th in the table in what many expect to be a transitional season.
“I’ve been in that situation.” Monk said. “When you’re a new manager and it’s your first year there’s a lot of stuff that’s going through your mind and as those years go on you get a bit more clarity on what you’re doing and how you put that in place.
“He’s a fresh, young English manager, which is great. I think that’s fantastic.
“He had a fantastic playing career and a lot of experience in terms of football and as you go on in management you get an idea of how you gain that experience of how to implement that.
“You can see what he’s trying to do and what wants to do. Good luck to him.”
Teesside-born Woodgate was the assistant manager of the club’s under-18 side back then and suggested the two shared little communication, with Monk preferring to focus solely on first-team matters.
In the weeks preceding Monk’s appointment he had been promoted to a coaching role with the first team during Steve Agnew’s interim spell in charge and admitted he had expected Agnew – later an Owls coach under Steve Bruce – to get the job permanently.
He also claimed the former Swansea boss had suffered from an ‘imbalanced squad’ with too many players during his time in the North East.
Speaking on Monk’s Boro tenure to TeessideLive, Woodgate said: “Our paths didn't cross much when he was at the football club. Very rarely did I see him.
“The maximum I seen him was three times in the training ground and occasionally in the canteen. He kept himself to himself really. He wasn’t familiar around the players. Some managers do that, others don’t.”
Asked whether his approach is the ‘direct opposite’ of Monk’s, he said: “I can't be someone I'm not if you know what I'm saying.
“I can't lock myself away and not see how people are, how staff members are. They're important in this football club, they're really important to me, how my staff are.
“It's not just about the players, it's about everyone being together and me showing them I'm a normal person who wants the best for the team and the football club.”