Playing at Wembley.
Kilbane made more than 300 Premier League appearances, won more than 100 international caps and even played at a World Cup before calling time on his career earlier this season, but yet never played a competitive game at the Home of Football.
He'll be working as a pundit in the Sky Sports studio when Southend and Leyton Orient clash in the second leg of their Johnstone's Paint Trophy Area Final and he has encouraged both sets of players to grasp their chance to appear in a Wembley Final on April 7.
And having made his debut in the Football League Trophy as a youngster at Preston, he says this competition has huge value for players in League One and League Two.
He told skysports.com: "When I started out, my first ever competitive start in football was over at Hull, playing for Preston in the Johnstone's Paint Trophy, so I'm fully aware of what it means.
"In the early stages you see teams field weakened teams like you see some of the top teams doing in the FA Cup, but when you get to the quarter-finals, the semis and obviously the Area Final, teams start to take it a lot more seriously because there's lots at stake.
"There's an appearance at Wembley for the clubs involved and both Southend and Leyton Orient haven't been in good form, both lost at the weekend and this is a great opportunity for them both.
"I never played at Wembley once in my whole career and it would have meant so much for me to play there. I was fortunate to get to a Play-Off Final with Huddersfield, but it was moved to Old Trafford because of the Champions League Final.
"You don't realise when your career is in motion that you might only have one opportunity to get there and you've got to try and grasp it with both hands because you might never get there again."
League Two side Southend are in pole position ahead of Wednesday night's second leg after Ryan Leonard's goal secured a 1-0 win at the Matchroom Stadium.
Kilbane is tipping the Shrimpers to make the most of home advantage, but says it's difficult to write off Leyton Orient, even though their hopes of a top-six League One finish have stuttered in recent weeks.
He added: "Leyton Orient are nine points off the Play-Offs at the moment and are probably there for a reason. They're not consistent enough to get themselves into the Play-Off places.
"I think they see this as their big opportunity to get some silverware and some success out of their season, so they'll be going to Southend with that in mind. When Russell Slade speaks to them before the game, I'm sure he'll tell them exactly that and will get them right up for it.
"But since the Johnstone's Paint two-legged Area Final was introduced there's only one team that have won the first leg and not gone through, so that goes against Orient.
"I watched the first leg and they had chances to go in front and to equalise after Southend scored. David Mooney missed a couple of chances and he'll be looking to rectify that.
"Paul Smith played really well and made two or three crucial saves in the match and as the team from the division above they should be going there with a chance.
"But Southend are at home, so it's evenly matched and it can go either way. You wouldn't be surprised whoever gets through in this tie and that's what makes it so intriguing.
"I'm going to go with the statisticians and go for Southend, having the home advantage with a 1-0 lead, but I wouldn't rule anything out in this tie."
Kevin Kilbane will be in the Sky Sports studio for Southend Utd v Leyton Orient, 7pm, Wednesday, Sky Sports 3 HD