A full six months before the hat-trick away to Inter Milan brought him international attention, the young Welshman scored vital goals in back-to-back 2-1 wins against Arsenal and Chelsea in April 2010, which greatly helped Spurs qualify for the Champions League in the first place.
Since then, Bale has gone from teenage prospect to one of the world's most coveted players via winning the PFA Player of the Year award in 2011.
Given such status, it is no surprise that talk about him leaving White Hart Lane after five years is constant, with a whole host of clubs at home and abroad reportedly keen on signing the 22-year-old for huge sums of money.
As Spurs face what looks likely to be a crucial summer, manager Harry Redknapp and chairman Daniel Levy have to decide whether it would be better for the club to keep one of their prize assets or to cash in on him.
Here are some pros and cons they will have to weigh up when making their decision.
It's hard to put a price on a talent such as Bale, but it's been fun trying. Differing reports have put his potential value at a huge £30 million, an eye-watering £50 million and a truly blockbusting £150 million.
We can dismiss that nine-figure fee for the bunkum that it is. However, given his age, potential and stardom, a price in the tens of millions is certainly not out of the question. This is especially true when you consider that Levy has a track record of driving a hard bargain, being able to extract the maximum revenue out of a star asset when Spurs decide to sell.
Losing Bale would undoubtedly be a wrench, but with the sort of money they would get for him Tottenham could reinvest by strengthening several other areas of the squad, not least at centre-back and in the striker department.
Bale is undoubtedly one of the most exciting players in the Premier League, but this season some of his limitations have been exposed.
Perhaps inspired by the Welshman's second goal of his brace against Norwich last December—which he scored after a rampaging run through the centre of the pitch—Redknapp took to fielding Bale in a more central role several times in subsequent games.
It would be both harsh and inaccurate to blame Spurs' poor run of form around this time on Bale's shift inside, but it is fair to say that he was nowhere near as effective in his new role.
It's not a crime to say that a player is not Cristiano Ronaldo, but the huge figures being thrown around Bale are based as much on his potential as they are on his current talent. If clubs eyeing up the player are not convinced that he can improve as much as they first thought, their offers are likely to be smaller or perhaps be cancelled all together.
Bale has become a real target for hatchet men out there who have no answer for his strength and quick turn of pace.
The winger was pilloried for his recent assertion that he is not a diver by nature, merely keen to avoid serious injury, but you can sympathise with him. Few other players have their ankles targeted with quite such relish.
That being the case—coupled with persistent yet unconfirmed rumours about his prohibitively short hamstrings which threaten to curtail his career—Bale could pick up a serious injury at any time.
A cautionary tale for Spurs is a reminder of what happened with Paul Gascoigne back in 1991.
Spurs had agreed the sale of their star midfielder to Lazio for £8.5 million—a world record at the time—before the FA Cup final that year, but in one of his increasingly common moments of madness, Gazza injured himself trying to maim an opponent. He missed the entirety of the following season while he recovered from his knee injury, and eventually moved to Rome for £3 million less than was originally agreed.
It may be stating the obvious to say it, but should Spurs sell Bale, they will be letting a great player slip through their grasp.
They may well turn a significant profit on their £5 million investment, but all those extra zeros on the balance sheet will not compensate for his absence on the left wing for the team from where he has scored 10 Premier League goals and set up another 10 this season.
It would be bad enough if Tottenham were to let Bale leave for Spain or Italy, meaning the chance of him coming up against his old club in the champions would only be a slim one.
But if the Welshman made like the vast majority of British stars and stayed at home, Tottenham would not only be weakening their own team but heavily strengthening that of a rival.
A major part of dealing with the loss of Bale would, naturally, be in replacing him. How many candidates are there who would be able to do such a thing?
Tottenham may well have, say, £40 million to spend on finding a replacement, but if they were to spend big on a star to fill Bale's role, it would beg the question why they didn't just keep him in the first place.
Similarly, as commendable as it would be for Spurs to repeat the process of bringing in a young prospect relatively cheaply and giving him time to develop, the intervening period of that player's progress would still see the team suffer.
Any young player who would be close to coming in and filling Bale's shoes immediately would likely already be widely known, and their current clubs would be only too aware of their young asset's value.
The other major repercussion of Tottenham selling Bale is that it could potentially open the floodgates for many of their other star players to leave.
Levy spent the whole of last summer doggedly refusing to acknowledge Chelsea's advances for Spurs playmaker Luka Modric, despite the Croatian himself publicly admitting that he wanted to leave.
The aim was to send a clear message that Tottenham were no longer a selling club. That message was not just meant for other clubs, but it was also meant to let the Spurs' own players know that their ambitions could be met at White Hart Lane.
Selling Bale now would render all of last summer's resistance worthless. Players like Modric, Rafael van deer Vaart and Kyle Walker may ask where Tottenham is the place for them and seek moves of their own.
Whether Bale stays or goes this summer will not only affect his own future, but potentially that of several of his current teammates and the club as a whole.