He did eventually break his duck at the famous arena when Sausalito Bay beat none other than triple Gold Cup winner Best Mate in the Supreme Novices' Hurdle of 2000.
Further victories followed for Nicanor, who beat another subsequent Gold Cup winner in Denman in the Royal & SunAlliance Hurdle of 2006, and last year when Go Native won the Supreme.
It is Go Native who is Meade's best chance of a winner again this year as he heads the Champion Hurdle market, and he also stands to win a cool £1m bonus put up by betting exchange WBX.com having won at Newcastle and Kempton already.
Meade is nonplussed by his Cheltenham record but, unlike many trainers, the Festival is not the be all and end all for him.
"I just think there is so much other good prize money to be won along the way that I owe it to my owners to try to win some of it. If that means they might not be at their peak in March then so be it," said the Co Meath man.
"Even when I've won there the press said Best Mate was unlucky, Denman wasn't at his best and Medermit would have beaten Go Native with a clear run last year, so I can't win."
However, with so much at stake, Meade admits to having changed his policy slightly with Go Native.
"We didn't train him through January at all. He ticked over and hacked every day but we slowed him right down to hopefully get him at Cheltenham spot-on," he said.
"If it wasn't for the bonus he might have gone for the Irish Champion Hurdle. Once he won at Kempton, though, I thought straight away we'd take him straight there to give him the best chance."
Go Native has been vying for favouritism since January as one after the other of the leading contenders seemed to drop away -- including then-favourite Zaynar being the joint shortest-priced loser in the history of jumps racing when turned over at 1/14 at Kelso.
Charles Byrnes' Solwhit advertised his claims in the Irish Champion Hurdle but did not see which way Go Native went at Newcastle and recently suffered a setback, while it has not been plain sailing for Punjabi.
Meade said: "I think Punjabi is getting forgotten again, you should never dismiss previous winners, and the only one we haven't a form line on is Zaynar, but you'd have to say he was disappointing last time.
Meade has, of course, gone agonisingly close in the Champion Hurdle before with Harchibald, who attracted more column inches than any other Champion Hurdle loser.
Having looked all over the winner in 2005, he could not get past the indomitable Hardy Eustace.
Carberry came in for some stick after that ride, but subsequent events proved no man would have won on him that day. Some have tried to draw a comparison with Go Native as he had his authority whittled down after the last at Cheltenham last year and at Kempton at Christmas, but Meade is adamant they are not the same.
"Richard Hughes came up to me after Kempton and said he was there far too soon, the run-in is longer than you think," he said.
"Paul said the same about Harchi when he won there.
"There may be some similarities between the two but what I will say is Go Native has more pace, it was Harchibald's jumping that made him look so good.
"We had some great days with (Harchibald). Funnily enough he's probably the best known hurdler in Ireland, more so than Hardy Eustace who won it twice."