Carlisle's appearance in this Sunday's JPT final is their fifth - a record for the competition.
If they can upset the odds and beat Southampton, they will officially become the most successful team in the competition's history.
So, with that moment of history in mind, our Fan Files turn their attention towards the Cumbrians.
United fan David Jackson has been following his local side from being a youngster in the late '80s.
Over the years he's seen many amazing moments following his side including goalkeeper Jimmy Glass's injury time goal to keep them in the Football League and a nerve-wracking penalty shoot-out against Aldershot in the Conference play-offs.
His worst period supporting Carlisle was the summer of 2001 when former chairman Michael Knighton seemed intent on running the club into the ground with the sacking of manager Ian Atkins and destruction of the squad.
So, Dave, you're through to the Johnstone's Paint Trophy Final this weekend. It's a competition where Carlisle have had had good success in, in the past. You must really enjoy it?
This is, I think, my 28th consecutive match in the competition. Since 1995, I think I've only missed six JPT matches - and most of them were because of a two year spell where I was working and couldn't get to games.
However, I'll usually go whether it's as part of an 800 crowd at Accrington, a trek to Chesterfield or a short trip to Morecambe. I just enjoy cup games on the whole so I go to most of them whether they're the League Cup, FA Cup or JPT.
I find cup games have a different aspect to them than league games. In a league match making sure you don't get beaten seems to be the sole main priority these days. Get a win if you can, but first make sure you don't lose.
When it's a cup game though, teams try to win. Even if you're playing away to a side two leagues higher you can see your club have a go and there's no pressure on losing the game.
I can enjoy a drama, stressed-filled second leg of the area final clinging onto a desperate lead as much as a first round game when you can sit in comfort with a small number of fans, no pressure, and just enjoy the game.
What do you make to sides then who don't the JPT seriously as a competition? Does it just add extra cup games that only generate money when you get to the final? Or can it liven up a mid-table campaign - as Carlisle are having?
On the club side of things, finances is what makes me wonder why clubs don't take it seriously, especially these days when finances are so tight.
I think we're going to make about £300,000 from the match, can many clubs in Leagues One and Two afford to toss that into the nearest dustbin?
I have also always thought cup games don't affect league performances. We have on three occasions got to the JPT final and also won promotion.
Birmingham, Bristol Rovers and MK Dons are all other examples I can think of who've done the same. Many losing area finalists also go up in the same season.
My main reason for the competition is because it's a memory. You can follow a side for 20 years and get good games and bad, but you only get a few lifetime memories in football.
This is what these days are for - memories you can look back on in five, 10, 20 years. I can still remember going to Wembley in the 1994 final.
I can still remember the trips to Cardiff - the Millennium Stadium, the match day, the whole weekend. These are things you can look on and say you where there.
Let's talk about your manager, Greg Abbott. He kept you up last season, he's got you into the top half this term, and through to the JPT Final too. He must be popular with the fans?
Considering achievement-wise he's done probably better than most in League One, he's not that popular.
The Wembley trip and a couple of recent wins will certainly buy him time to get to the summer and try again, but he's been up and down.
Certainly, I'd be honest and say he's done better this season than last. Last term was horrendous.
He inherited a squad with no morale and no teamwork - added nothing and then annoyed fans with stupid comments, bad interviews, and poor signings. How he survived to this season I am unsure, as no fans wanted him.
This season has been a mixed bag. I think on two occasions he has been just a defeat away from the sack with 95 per cent of the fans wanting him ousted. Only for him to then get the vital win at the right time to keep him plugging along.
The cup runs have been his saving grace this year - giving fans big days out to look forward to and also making the club about £500,000.
That's probably made a few fans warm to him, but I don't we're much better than last season, the league is just much, much worse.
We secured survival to me last midweek [a 1-0 win over Yeovil] so he should fair better come the end of the season. His away tactics are terrible though - he likes to go for a 0-0 draw away from home.
They just don't make you want to go and watch us away from Brunton Park. Plus, we have needed a big, stronger striker for about two years and then, finally, after a year of rubbish we find in Vincent Pericard.
When he went though, he didn't bring in a replacement having said he would do. Now he's been forced to because of injuries, has brought in another striker who fits the bill and, hey presto, two wins in two since then!
It's these bits of bad management - like dropping one of our best players for nine games in-favour of his favourites - and terrible interviews which turn you against him.
He's got another season to try and win fans over though, so we'll see.
So, looking ahead to Sunday's final. Do you think you can cause an upset and beat Southampton?
Yes, I think we're destined to win this one. We are one win away from being the best Football League Trophy side ever. We have been in the most area finals with seven, the most finals with five, and just need to get joint-most wins.
Against us is a team with a lot of money, and we have not got a good final record.
However, they've lost a few players and the big thing with our squad is that it's filled with ex-higher league players like Ian Harte, Scott Dobie, and Graham Kavanagh.
Wembley usually brings out the best of these players and if you can get them performing like they did in the prime, and then guys like Peter Murphy and Danny Livesey performing as they can - we have a strong side on the day.
Away from Sunday, ten years ago Carlisle were battling to stay in the Football League, now you're spending a fourth straight season in League One and only missed out on the Championship in the play-offs in 2008. Can you make the step-up to the second tier in the future.
No. Football has changed too much ow and it's who you have financially, rather than the size of club, which dictates how you do. We have no rich owner - just local businessmen who keep the club ticking over.
We have made a profit in about five out of the last six seasons, which is good, but the one bad season last year - when we made a loss - nearly crippled us.
We just don't have the backing to afford making huge financial losses over two to three season to build a top League One side.
Leagues One and Two will always be our level. However, considering in the last 20 years we've mostly been struggling in League Two, we've progressed.
Your club will always be famous for that Jimmy Glass in 1999 of course. Do you ever feel you could follow the Cumbrians for another 50 years but never experience a moment that will surpass that one.
I don't think so, because I think I've seen a couple of moment just as good.
In terms of the actual context then you're probably right. It will never happened again because it's a set-up that was once in a lifetime.
Glass came in after the transfer deadline had passed due to our loan keeper at the time being recalled. This was the first ever 'emergency loan' used - and that rule only came in at the start of that very season.
Our game was also only still going after Scarborough's had finished because, by chance, a Plymouth player broke his leg during the game so this left us knowing what needed to be done.
All the situations just point to fate work a bit of magic to set up a moment that will never be repeated. However, the penalty shoot out at Aldershot was cracking drama.
We were 3-1 down with only two penalties left each. They had to miss both and did, we had to score both, and did. Then we won in sudden death.
Matt Glennon's injury time penalty save at Mansfield which stopped us being relegated - for that weekend at least - had the same impact at the time.
The Jimmy Glass moment will always be looked back on though because it was the right moment at the right time with a unique set-up and the perfect conclusion.
You've seen your team play in three different divisions over a long period of time. How do you think the game in the lower leagues has developed both on and off the pitch over that time?
Facilities would be the main thing. When I started going, away ends were a scabby bit of terrace with a toilet that was a wall with a gutter at the bottom. The food was non-existent and you were lucky to ever get away seats.
Grounds have drastically changed. I missed a lot of the character of the old grounds - and were tied to their own clubs and felt like they were their grounds - but the facilities were shocking.
As for the football, well, it's improved a lot to be fair. In the early 90s it was a long ball era of sides who came to your ground to sit back, whack your players to bits, and hoof the ball to a big lump up front to nod down to the faster player next to him.
Now, teams do try and play a passing game. It isn't always perfect, but teams do try and get some footballers in.
I do think wingers years ago were better than those these days. I think that is a general thing in football too as, because top sides have found foreigners better for the skillful positions, it's seen a drop in quality in those positions from the top flight youth players.
Which means less for us, better strikers and defenders have to look like The Incredible Hulk to succeed.
I think there are more tactics in the game now compared to back then, but I think teams are more negative these days than they were years ago.
Also, I think atmospheres were a lot better years ago and managers had more links to fans too because in them days managers were not sacked within a season.
Finally then, Dave, what's the best thing about being a Carlisle United fan?
This is going to be only the second time in 22 years I've seen us finish mid-table, and even then it's a season of big games, cup finals and exciting moments.
So, I'd say the fact the best thing is that, whether good or bad, we usually have something happen every season. Maybe they'll give me a heart attack one day, but it's better than having nothing to talk about during each season.
Dave, thanks for talking with us. Good luck on Sunday and for the rest of the season!