In 2019-20, Woodgate led Boro to a 17th place finish in the Championship in what was his first season in senior management.
Despite getting verbal assurances from Middlesbrough chairman Steve Gibson, the former defender was relieved of his duties shortly after the Championship resumed following a Covid-19 suspension.
“It was the start of Covid I came in,” Woodgate said when discussing his dismissal at The Riverside. “I remember we played Charlton and we won 1-0 [in March 2020].
"Previously I had a meeting with the chairman, my staff and the chief exec and he said ‘I’ve got one thing to say to you Jonathan – if we get relegated, you’re getting us up and if we stay in the league, we are going to rebuild. There are seven players out of contract and you’re going to rebuild it’.
"Perfect. So we went into Covid, come out of Covid and got beat by Swansea 3-0 and two days later, I’m sacked.
"It was a really difficult moment, the team I supported as a kid, played for and then I was the manager, and it was the perfect job.
"Telling my kids was the hardest thing, because my son just burst out crying because he is a Boro fan. That was really, really tough.
"I was embarrassed as well. Embarrassed that I’d lost my job so early on in my management career.
"If your first job doesn’t go to plan, it’s highly unlikely that you’re going to get a second one. Luckily enough I did, but it’s that feeling of not being able to do the job that you know you could have done.”
Woodgate returned to management on a short-term basis the following season at AFC Bournemouth, leading the Cherries to a play-off position in the second tier.
But he admitted leaving Boro under the circumstances he did was ‘tough.
Speaking on the Original Penguin X Campaign Against Living Miserably Under The Surface podcast, Woodgate added: Looking at all the players I was gonna sign, trying to build for next season with seven players out of contract, the chairman said he was gonna back me in the summer.
"I was absolutely gutted. It was a drive home and I can’t remember getting home. I cannot remember getting home. I was on autopilot thinking ‘what has happened here’.
“Boro was my dream job. I was meant to be going the Liverpool v Spurs Champions League final, but I had to do the interview so my Mrs went with my son. Who is going to turn doing their dream job with their home town club? Didn’t work out.
“I got a lot of abuse, from the fans. I’m not intellectually clever, quite basic, and I get called a hell of a lot of names – he’s thick, he can’t talk properly. I lost a bit of confidence to be honest with you just as a person. What’s helped has been doing a lot of radio work for 5Live, and started to get a bit of confidence back.
“It was tough. If you get a lot of abuse online – if you shoot so much mud, some of it sticks.”