In the role of club and company secretary, he has had a closer view than most at the highs, the lows, the heartbreak and those frantic, last-minute, deadline day phone calls.
His quarter of a century in football, which included five years as financial controller at West Ham before joining Wolves in 1996, coincided with perhaps the most transformational periods in the history of the game, the arrival of all-seater stadiums, the formation of the Premier League and continued widening of the gap between the haves and the have-nots.
To supporters, he has been a familiar face, if an unfamiliar voice. Not the type for making public pronouncements, Skirrow's work has tended to be done behind the scenes, a vital cog in the Wolves machine. He would not have wanted it any other way.
"I never wanted the chief executive role," he remarks at one point. "Club secretary, when I was a lad, was a very well-respected role. I didn't aspire to be the No.1 with all the added pressure and the need to be the mouthpiece. I was always happy to be able to go into a pub or restaurant and be largely unrecognised."
Meeting Skirrow, who retired earlier this month, it does not take long to understand why he has come to be so well-liked and respected.
Play-off joy after a stitch in time!
Richard Skirrow's favourite memory of two decades at Wolves was also his most stressful.
The 2003 Division One play-off final victory over Sheffield United at Cardiff's Millennium Stadium, brought joy to supporters as they returned to the top flight after 19 years away.
Yet for club secretary Skirrow the occasion brought with it numerous complications concerning ticketing and a late, unexpected change of goalkeeping kit.
"Cardiff was amazing but you could write a book about it with the various issues," he said.
By some distance the strangest issue occured when the referee deemed both goalkeeper kits were too similar and asked Wolves to come up with an alternative.
Born in Yorkshire and raised in Manchester, his down-to-earth, easygoing demeanour evokes those northern roots. Meanwhile a razor-sharp memory plucks out piercingly vivid memories, from the 2003 play-off victory at Cardiff to Robbie Keane's debut and the joy of a last-minute Steve Bull winner at Bramall Lane. Through the ups and the downs working for the club has remained, he says, an 'honour and a privilege'.
For owners and a succession of managers, Skirrow has not only been an administrator but a sounding board, a friend and, where Mark McGhee was concerned, a sometime music critic.
"I've got on well with all managers but I probably socialised with Mark more than anyone else," he says. "I like my music and so did he. Mark would bring in his latest CD and say 'have a listen to that'. For some reason I always remember him bringing in a Hootie And The Blowfish album which is not exactly mainstream."
Clearly, there is a fascinating book to be written, not that Skirrow – fiercely loyal to colleagues both past and present – is ever likely to write it.
That does not mean he is prone to
sugar-coating or unwilling to recognise the failures of the past 20 years. When Skirrow arrived at Molineux in November 1996, having been recommended by outgoing secretary Matt Finn, Wolves were seen as a club that was 'going places'.
The fact they have never managed to arrive at the destination is a chief source of frustration.
"I came to Wolves thinking there was a more chance of medium to long-term success here than at West Ham," explains Skirrow. "Wolves seemed to be on the cusp of big things.
"In my 20 years here, we have only had four in the top flight and that is very disappointing. I think we have many reasons to look back on what we have done with a bit of pride but that is not a satisfactory playing return, I would say.
"That is not an attempt to distance myself from any blame, far from it. But when you look at Stoke and West Brom, we should be trading blows with them. Leicester and Wolves are a great match in terms of size of club and support, the whole DNA.
"Leicester had their time in the third tier. But they have now won the Premier League."
Having spent more than 20 years of focusing on the fine detail of player contracts and organising life around the fixture list, Skirrow admits it will take time to 'emotionally disentangle' himself from the job.
He will remain, however, a supporter. Catching the end of the Best, Law, Charlton era at Old Trafford made Manchester United obvious recipients of his affections as a youngster. Now, Wolves are in his blood.
"You can never say it means more to you than the fans," he said. "But it is different, when you are in it five, six or seven days a week you do feel it. You can't switch off.
"When you are in a senior position you do feel entirely wrapped up in the ebb and flow of results.
"There are many times I have come back into Wolverhampton on a Saturday night or a late Tuesday and, if we have lost, you do feel embarrassed.
"Your mind automatically goes to the thousands of people who have done the same thing, in coaches, private cars and who didn't have a nice meal beforehand. You do feel the responsibility."
Skirrow's desire to see things from the supporter's point of view has seen him build relationships with a number of groups, including London Wolves and Daventry Wolves. He's also been a trustee of Wolves Community Trust, helping to steer the trust towards charitable status.
"I have always been keen on how we as a club interact with supporters and with other clubs – the 'ethics' of Wolves for want of a better phrase," he said.
"I am proud of the way we conduct ourselves by and large. We try to get involved in Wolverhampton and what is going on within the city. I've always regarded us – without being boastful – as the biggest show in town.
"That means we have a duty to act accordingly and to get involved in things and I think we compare very favourably in comparison to a lot of other clubs. I am proud to feel that we have acted very properly during my time here."
Skirrow, who lives in Stafford with his long-term partner Jane, intends to spend retirement doing the things an all-consuming job in football rarely allows the time for.
There are clearly things he will miss, though the transfer window – another of the game's developments during his time at Molineux – is not one of them.
"For a football administrator, the transfer window is not a good thing," he says with a smile. "We have had some ridiculously late shouts about potential deals. For a period it becomes live and stressful and people are asking, can you do it?
"I won't miss that at all. On August 31 this year, I shall make a point of being somewhere, preferably outside on a still balmy evening with a glass of something, toasting my absence from being involved in it."
There will still be trips to Molineux, though not every week. "That would rather defeat the object of retiring!" he jokes.
Skirrow will now join those in the stands, seeing if Fosun can deliver the sustained success which has stayed frustratingly out of reach.
"They will learn from this season and are very committed to making Wolves a successful and established Premier League team," he said.
"I can't see why that can't happen – it won't be easy but with the right recruitment and people in place, and Fosun's commitment, we should see progress.
"I will enjoy being in with the fans – that is how I started watching football and I really enjoy it."