The Red Rose county famously fell 24 runs short of winning the County Championship title against Surrey at the Oval in September.
It was ultimately one of the reasons that featured in the 31-year-old's decision to resign as captain after three years in the role - even though the main one was his lack of form with the bat.
"It is without doubt the biggest disappointment," he said.
"The C &G Final in 2006 was also a huge disappointment because I know that we should have won that game.
"But the emotions that we had all gone through on that day at the Oval. I genuinely, believed that we were going to do it. I think there was a real positive feeling throughout the whole team right through the day.
"We sat there in the changing room all day thinking `We're going to pull this off, we're going to pull this off.'
Dejection
"So the dejection at the end of the day was something that I don't believe I will ever feel again."
Since attempting to chase down that 489, Chilton has seen Stuart Law replace him in the Old Trafford hot-seat.
And it is a move that he whole-heartedly supports: "Hopefully he can get the guys pushing to go that extra step," Chilton continued.
"We did come close under my reign - and we have got a good platform, we have got a good quality of player.
"He is one of the best players that I have ever played with. Hopefully his performance will continue to be as exceptional as it has been."
Chilton looks back fondly on his reign, describing it as a `proud three years.'
At last week's Pro Arch Series launch in London for Lancashire's pre-season tour, Sussex bowler James Kirtley saluted Chilton's captaincy credentials.
"He led a very fine side - and his record as captain, although it might not involve any trophies, is a very fine one in terms of games won," he said.
Chilton added: "I know that my win per centage was very high. I know it is not just down to me, but it is down to the quality of the side as well.
Different
"We played a fair amount of good cricket - certainly in four-day cricket. I thought our quality of play was high, but you just have that disappointment that you are nearly men I suppose."
"Second in one year, 20 runs short in another, beaten in a final in another. It could have been so different, we could have gone down in history."
The former Manchester Grammar School boy has also become a father for the first time, with the birth of his daughter Bethan Rose in October.
"I am just loving it really - it has been an awesome few weeks," he said, confirming that he has also been on a three-month spell with the Yorkshire Bank.
"I have been doing a bit of work to get some experience of something else. It has been a good experience - helping me to take a step back from the game. It makes you value your time at the cricket a lot more because you realise how lucky you are.
"Hopefully that, and having Bethan, will help me to free up my cricket and perform."
Chilton only scored one century at the top of the order last season - and knows that his form with the bat must improve if he is to partner Paul Horton in 2008.
It was the main reason for relinquishing his leadership duties, and has vowed to come back stronger.
"That's my No1 prority now. I have to accept that my standard wasn't quite good enough," he said.
ENGLAND have agreed to play three one-day internationals against Ireland over the next five seasons, starting in 2009.
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my blackest day was when they decided to make you captain, then keep you on again this season as a batsman.
Everybody apart from the lancs board knew who should have been made captain
Stuart Law is now captain and about time too , hope he keeps going for a couple of seasons .
Imagine if he would have been captain for the past 3 years .
Mark Chilton would have concentrated on his batting .
Don't forget P Woodhouse , MC was touted as a possible england opener a few years ago . He will come good , i am sure .
the word was that Law did not want the captaincy then and proposed chilton. Pity, but let's hope better late than never. Biggest joke was chlton in 20/20