Annagh United manager Dean Smith has managed to get his hands on the Bob Radcliffe Cup five times during an illustrious playing career with Loughgall and Coagh United, but he insists leading his current side to glory in this year's Boxing Day final (Lakeview Park, Loughgall, 11am) would top the lot.
Smith is preparing to do battle with his old Loughgall team-mate and the club's current boss Brian Adair in a showdown where Loughgall are the clear favourites, despite the fact that they are struggling near the bottom of Belfast Telegraph Championship One, while Annagh are in the top four of Championship Two.
And while the Annagh boss is only too aware that the odds don't favour his club against the 12-time Bob Radcliffe winners, he knows they can also use that to their advantage.
He said: "It is one of those games where we have nothing to lose. There is no pressure on us.
"I know Loughgall haven't been going so well lately, but I think they are in a bit of a false position. I looked at their team-sheet on Saturday, and they have quality from one to 11, and throughout their squad. Brian will turn it around."
However, Loughgall's problems won't be in Smith's mind come kick-off in a game he would dearly love to win.
He added: "Without a shadow of a doubt this would be the best win of all. I have experienced what it's like to win this competition, and I want the players to get the same. Outside of the Irish Cup, it's the biggest competition in my book.
"There are people who do so much good work for this club, and they deserve to be rewarded for it."
Meanwhile, Adair isn't reading anything into the current standings and is bracing himself for a challenging encounter.
"Make no mistake, this is going to be a tough game. The fact that we're in Championship One and they're in Championship Two makes no real difference. They've a squad full of top players, some of whom have won cup finals and played in Europe before, so we know it will be difficult.
"If you look at their results, they're the in form team, where as we've had a frustrating start to the season. At the end of the day, I have to carry the can for that, but I'm confident we can go on a decent run and turn things around."
And like his opposite number, Adair is looking forward to meeting up with his old team-mate.
He said: "I know Deano very well and I've nothing but respect for him as a friend and as a player… he is somebody I have a lot of time for.
"He's like me, he's a real winner and he will want to win the trophy for Annagh. We're good friends but come Friday we will be in opposite dugouts and we will be doing everything we can to get one over on each other."
In another major Boxing Day final, Ardstraw will be looking to fly the flag for the Northern Ireland Intermediate League when they take on Limavady United for the Craig Memorial Cup (Fortwilliam Park, Tobermore, 11.30am).
Gary Simpson's Ardstraw are contesting the final for the first ever time while their Championship Two opponents are bidding to lift the trophy for a seventh occasion.