Despite such inauspicious beginnings, the Halifax-born goalkeeper has gone on to enjoy a fine career.
Two years in the Premier League plus a couple of Cup semi-final appearances are the clear highlights for Kenny, who earlier this season reached the milestone of 600 appearances and shows no signs of letting up.
“As you get older, you see people retiring through injuries and so on,” said the 35-year-old to the Yorkshire Post ahead of today’s eagerly-awaited encounter with Middlesbrough at Elland Road.
“But I speak to a lot of ex-players and they all say the same, ‘Play as long as possible’. I want to do just that.
“The thing is I love playing football. I think you do appreciate it more when you have worked for a living. I did four years as an engineer (before signing for Neil Warnock at Bury in 1998). And before that, I did a bit of packing.
“Players who come through at a big club from a young age maybe don’t know or even realise there is another side to life. They don’t ‘get’ the real world.
“I might not be the best trainer these days but I know how to best prepare myself for a Saturday. How to get in the best mental state and so on.
“I also realise just how lucky I have been and want to play on well into my 40s. I love playing as much as I ever have.”
Kenny’s state of mind is an indicator of not only his enthusiasm but also how happy a place Elland Road has become of late.
Three victories – the most recent of which was a 4-2 hammering of Charlton Athletic at The Valley – in four outings mean United go into today’s meeting with the Boro sitting just one point adrift of the play-offs.
Talk of possible buyouts and returning legendary figures may have dominated the agenda of supporters in recent days but that has done nothing to deflect the attempts of Brian McDermott and his men to keep climbing the Championship table.
As someone who has twice previously won promotion to the top-flight, Kenny appreciates better than anyone at Elland Road what is involved in succeeding at this level.
“It can be really unforgiving,” said the United goalkeeper when asked about the Championship, a division he has seen plenty of since joining Bury, who were then of the second tier, from Bradford Park Avenue.
“As a division, it is much stronger than it used to be. The parachute payments have made a big difference, though probably the standout thing about the Championship in recent years is how anyone can beat anyone else.
“A few years ago, at QPR, we were well clear at the top and went to Scunthorpe, who were bottom of the league. It was quite late in the season, maybe early April.
“Anyway, we were winning 1-0 only for Scunthorpe to hit back and eventually thrash us 4-1. It could have been 7-1 in the end. They totally battered us.
“And yet just a few weeks later, we won promotion and Scunthorpe were relegated. That shows how mad things can be in this division.
“You only have to look at ourselves this season for more proof of that. We went five or six games without winning not so long ago and there was a bit of negativity about.
“But now things have changed round completely. There is a buzz about the place and it is great to see. That probably hasn’t been there since I joined, if I am honest.
“I was surprised by how downbeat things were after I joined (in the summer of 2012).
“I was really excited about coming here. Leeds are a massive club but there just didn’t seem the buzz from supporters and that was a shame.
“Obviously, the season petered out as well and that caused quite a flat atmosphere. But now there is such a better feel about the place, compared to last season. We just need to stick at it.”
Today will be Kenny’s 617th senior appearance, an impressive tally considering the painful start his career got off to with Bury when an unfortunate collision with the knee of Gillingham’s Nicky Southall left the League debutant out cold on the opening day of the 1999-2000 season.
He recovered from the early clash to help the Shakers to a 2-1 triumph and before long rave notices were attracting the attention of a host of clubs.
Warnock, by now in charge of Sheffield United, eventually won the race for Kenny’s signature in 2002.
He said: “I remember being told at Bury ahead of my debut, ‘You have six games to prove yourself’. That was pressure but things went well and here I am all those years later still lucky enough to be playing.
“I can’t wait for the Boro game. Elland Road is an amazing place to play.
“I always thought that, even when an opposing player. I remember coming here with Sheffield United and QPR, and every time the crowd would be up around 30,000.
“It should be the same against Middlesbrough and we’ve already seen this season, in the win over Brighton on the opening day, what a big help a crowd like that can be.”