Now the striker is determined to sample the good times, when they finally arrive at Ibrox once again.
While the Light Blues were racking up league and cup wins under Walter Smith, Little was often consigned to a place on the sidelines as millions of pounds of talent filled the 11 jerseys on a weekly basis.
In the club's darkest days, the silver lining appeared for the Northern Irishman.
He has taken his belated opportunity with aplomb, hitting the goal trial in Scotland's lower leagues to play a major part in the rebuilding process that Ally McCoist's side are undergoing.
Rangers have some way to go on their journey back to the top and Little, who is out of contract in just a few months time, hopes he will be given the chance to finish what he has started.
"I am up at the end of May," the 24-year-old said.
"There is a clause where I have a one-year option if I play a certain amount of games.
"I would be very keen to stay and hopefully the club will have me. There have been no discussions.
"My aim would certainly be to stay at the club. I waited a long time to get my chance.
"In the last year-and-a-half or two years I have got my chance and I have been pleased with how I have done.
"I would like to stay right through to the Premiership and Europe.
"It is not up to me. I would hope discussions start soon. I will wait and see. I would love to stay."
Despite the arrival of Jon Daly and Nicky Clark this summer, Little has maintained his place in the Gers attack as his strike partner last season, Lee McCulloch, has starred at the other end of the field.
The nine new faces in the Ibrox changing room are already having a profound affect, with McCoist's side waltzing their way to the top of the SPFL League One standings in stunning fashion.
Little could have found his place under threat this time out but he has proven to be a valuable and reliable source of goals once again.
And the striker credits an end of season talk with two of his mentors for his superb showings so far this term.
Little said: "I had a good break over the summer. It was the first season I had played 36 games.
"I had a good holiday but I came back pretty fit, like the rest of the boys.
"Ian Durrant and Kenny McDowall spoke to me and the other boys at the end of last season and said it would be different this season, that there would be a lot more competition for places and if you wanted to be in the team you would have to be at your very best.
"That stuck in my mind over the off season and in pre- season that if I wanted to get a starting jersey I would need to be performing.
"I have been doing everything possible since getting the jersey to keep it. Like everyone in the team, that is the aim, to stay in it."
Rangers head into their clash with Ayr United at Somerset Park tomorrow afternoon top of the table and full of confidence following their 8-0 route of Stenhousemuir at Ibrox last weekend.
Even at this early stage of the season, the improvement from last season is noticeable to see for the Light Blue legions and Little admits he always had faith the Gers would shine this term.
"We knew we would be a much better team this season, we could see that in pre season," he said.
"The players that have come in, every one of them has made an impact and has put competition for every position on the pitch.
"But at the same time, we know there is a slip-up just round the corner waiting to happen if we don't prepare ourselves properly and turn up in games, like at Forfar."
With seven wins from seven games already to their credit, Rangers have laid down an early marker of their intentions in League One.
McCoist's side have outclassed their opponents so far as they have hit the goal trail and entertained fans.
Only Forfar have stopped the Light Blues in their tracks so far this season, the Loons ending Rangers' League Cup ambitions at the first hurdle.
And Little insists there is no reason why the Gers' unbeaten run can't be extended for the remainder of the campaign.
He said: "I think we can (go unbeaten). I don't see why not. We need challenges, we need things like that to aim for.
"We certainly won't talk about it but personally I don't see why not. We are capable of winning every single game so why not go and do it?"
The next side out to cause a shock and defy the champions another three points is Ayr.
With the trip to Somerset Park tomorrow seeing McCoist's side hit the road once again as they target an eighth straight League One triumph.
Their progress will come to a halt next weekend, however, with the club making the call to postpone their Ibrox fixture against Dunfermline due to international call-ups.
Little could yet be recruited for national service if he is selected for Northern Ireland's two final World Cup qualifiers.
And the Enniskillen-born strike star admits he has mixed emotions about the postponement of the Pars clash.
Little said: "I am on stand-by but I am desperate to be involved with Northern Ireland. We have Azerbaijan away and Israel away.
"I wouldn't be surprised if there are a couple of call-offs and I might get in there. It would be brilliant for me.
"On the flip side of that, if I was to miss a (Rangers) game, I would be disappointed to not be able to play for Rangers.
"For me it is a good thing but I understand it is bad for fans who have booked trips, especially from where I am from.
"I'm sure there are ferrys booked and flights booked."