Now happily retired from the game he can look back and smile but the admin error that blighted Phil Whelan’s Boro career was no laughing matter at the time.
Indeed, the defender would quickly become accustomed to quips about Keith Lamb’s fax machine.
Not that Boro’s chief executive was in the wrong.
It was January 1995. Boro were in need of defensive cover. Phil Whelan, at Ipswich at the time, was open to the offer of a move.
In fact, the chance to play for Bryan Robson was something the 23-year-old was never going to turn down.
The strapping centre-half didn’t have much time to think about the move after discovering Boro were interested on deadline day but didn’t need any convincing.
He took a phone call at 2pm and learnt a fee had been thrashed out by the two clubs. By 4pm the deal was done and he was a Boro player. Or so he thought.
This is where the fax machine comes in. But not Keith Lamb’s.
“I think it was Steve Vickers who’d got a two-match suspension and Boro wanted to bring in cover at the back,” says Whelan.
“The two clubs had agreed a fee, I spoke to Bryan Robson on the phone about a few things and agreed terms by which time it was about 4pm.
“As far as I was concerned the deal was done and I was delighted. The papers were then faxed to the FA but there was an issue there and they didn’t receive the papers until 5.30pm time.
“It wasn’t until the next day when I realised what had happened. I was on my way up to Boro when I got a phone call to say there’d been a problem.
“I got to the training ground and they told me I wouldn’t be able to play until the following season.”
It was far from ideal for the big centre-half.
While Boro finished the job in such impressive fashion and won promotion to the Premiership, Whelan was a frustrated spectator in the stands - delighted for his team-mates but unable to shirk off the feeling of disappointment that he hadn’t been able to play a part.
“When we got promoted we didn’t sign any more defenders so I thought it would be an opportunity for me but the manager started with the players who had played for him the season before, which you can understand.
“Getting promoted that season was fantastic for the club but there was a little niggling feeling that it could have been me on the pitch playing a part.”
Regardless of who you speak to, all of those who were part of that 1994/95 title winning side speak of a special time for the football club.
Those who attended the recent reunion of the squad at the Riverside, including Bryan Robson, John Hendrie, Derek Whyte, Craig Hignett and Curtis Fleming, all look back on that campaign and the first two seasons in the Premier League as a stand-out time in their career.
Whelan is no different. He went from joining a club gunning for promotion to playing alongside the likes of Ravanelli and Juninho in less than two years.
“It was unbelievable,” said the 42-year-old.
"An incredible time for the club.
“I came in in 1995 and it was about that time that everything just exploded, the town was absolutely buzzing.
“I’ve never known anything like it anywhere else.
“The players who came in, you honestly couldn’t have made it up.
“Ravanelli, Juninho, Emerson, these are players who every club in Europe would have wanted to sign.
“Looking back, I think it was the signing of Nick Bamby that started it all off.”
And Whelan is in no doubt as to how Boro attracted the superstars to Teesside.
“Steve Gibson is a man who is completely and utterly passionate about his football club, you couldn’t fail to get drawn in by his passion,” he said.
“But the reason for all of those players coming to the club was Bryan Robson, players wanted to play for him.”
“He was a fantastic bloke. He was still actually a player when I signed and he still wanted to be on the pitch.
“On the pitch he was so passionate, was never afraid to tell you exactly what you should be doing.
“Off the pitch he was a really nice bloke but at times he could have maybe done with that edge that he had when he was on the pitch.”
Whelan says he has a soft spot for all of his former clubs so would love to see Boro and Ipswich win promotion this year.
This season, he says, is by far Boro’s best chance of getting back to the big time since they suffered relegation six years ago.
From the football pitch to the classroom. He’s got some incredible stories to tell the youngsters. For Mr Whelan is now a primary school headteacher.
While other players deliberate over whether or not to go into the coaching side of the game, Whelan had an accounting degree to fall back on when finished playing.
But he admits he didn’t fancy going from spending his days on the training pitch to sitting in an office all day, every day.
Instead, a chance conversation with a friend who was a teacher led to him being invited into a school for the day. He was hooked.
“I had an operation in January 2003 when I was at Southend and my contract was up at the end of the season,” he explained.
“That’s when I knew I would have to call it a day. It was my fifth operation.”
He moved to Cheshire the year later where he got his first teaching job and just over a decade on he’s now the head teacher at Millfields Primary School, in Nantwich.
“I love it,” he beamed.
“There’s a lot that transfers from football to education.
“Motivation is the most important. If you can master self-motivation and realise you are the most important person in your future you’re well on the way to success.
“There’s things I miss about playing football.
“If you watched me at Boro then you’ll know playing the game was never my forte so training was always hard work,” he laughed.
“The thing that I miss most is going into the training ground every day when you’re a young lad and having an absolute ball.
“There’s so much banter flying about and it’s brilliant.
“I can’t imagine any other career when you get that on a daily basis.
“But I love what I’m doing now.
“I plan to coach the football team and I’m very keen to raise the profile of sport within school.”
He never went into management but you can bet his primary school team will be successful.
There aren’t many youngsters who can quiz their headteacher on what it’s like to play alongside a World Cup winner, after all.
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