Media playback is not supported on this device
It is the blue-riband race of the most prestigious meeting in the sport - but only once has a female jockey ridden in it, and that was more than a generation ago.
Back in 1984, Linda Sheedy did not reach the finish on board 500-1 outsider Foxbury, so Devon-based Lizzie Kelly is determined to smash through another glass ceiling.
Not that she goes along with the idea that women have it tougher in the saddle than their male counterparts.
"A lot of the time I don't think girls push themselves to the extent that I was willing to push myself," she told BBC Points West.
"I wanted to dress like a male jockey, with all the right gear and everything, and you've got to really strive to achieve just as much as they are.
"I had to do more to fit in, and look right, look the same as all the lads."
The 23-year-old rides Tea For Two in the big race on Friday and while she is comfortable with being viewed as a trailblazer in sport, it certainly is not something the conditional jockey burdens herself with.
"If anything I do is good for women in racing or women in sport, I always think that's a good thing, but it's a total by-product," added Kelly, who has been part of BBC Radio 5 live's commentary team at the festival.
"I'm selfish, I'm doing it for me, I'm not doing it for females in general - I'm doing it because this is what I've worked towards and dreamed about since I was a kid.
"It's great if people look at me and think 'I can do better than her' - go on then, come on, let's do it, because why not?"
Such a comment is typical of Kelly's go-getter personality - and she has already made racing history, by guiding Tea for Two to victory in the Kauto Star Novice Chase at Kempton in December 2015 to become the first female jockey to win a Grade One jumps race in Britain.
"When I left university I just thought, I don't want to sit in an office from now until retirement," she said.
"I was 21, and I just felt that I could sit in an office for 20 years in 20 years time, and that was the push.
"I thought you have to take your chances while they're still there, and I'd have regretted not giving it a go in later life if I hadn't."
Aside from the overriding gender theme, which Kelly accepts as a big talking point ahead of race day, it is a family team that surrounds Tea For Two.
The eight-year-old is trained by her stepfather Nick Williams in the village of George Nympton, near Barnstaple, and co-owned by mother Jane Williams, who says her daughter wasted no time getting into the saddle.
"She was so young that she was riding in the arena, they had letters on each corner of the arena, and she didn't actually know what the letters were, she was that young she couldn't read," said Jane.
"She hasn't been given anything - she rides for us and we run a business, and if we don't get the success then we won't be here in years to come.
"It's not a gift, she's earned it and I feel very proud that somebody can be that dedicated that they actually make it work."
Described as being "a jockey for the big occasion" by her step-dad, Jane says she is more worried about her horse's mentality on the day than that of her jockey.
"The horse is exceptionally temperamental - he likes going to Exeter, but I'm not sure he particularly likes going to Cheltenham," she added.
"We've got to get there - it is a concern because he will have a lot of stage fright that day I suspect, because the festival is completely different to any other race meeting."
Though Kelly and her family are proud to be making history at Cheltenham, they are looking to do far more than just make up the numbers.
Tea For Two is a 66-1 chance with most bookmakers - but Jane Williams is surprised that the odds are so long and is targeting a place.
"First of all we've got to get round, just jump round - if I came fifth or sixth I'd be absolutely over the moon."
The final word goes to Lizzie herself; how will she feel waking up on Friday morning?
"You think I'm going to sleep?" she responds.
"It's our first Gold Cup, it's his [Tea For Two's] first Gold Cup, my first Gold Cup, mum's first Gold Cup - so I think the only way I can try to feel is excited."
Interviews by Damian Derrick, BBC Points West
If the Cheltenham Festival is 'the Olympics of horse racing', then the Gold Cup is the equivalent of the 100m finals.