Plenty of us punters love letting our winnings 'ride' by rolling the lot onto the next race (whether that be at Toowoomba gallops or Pinjarra harness).

These three gamblers, however - courageous or crackers depending on your point of view - raised the stakes to a whole new level...

Each starting with only modest bankrolls, the three would come to wager some extraordinary dollars on the racetracks of Australia, risking it all as their wealth (and heart rates) increased with each passing win.

But which of them knew when to walk away?

Punter #1: “The Woman In Black”

The mysterious Woman in Black was Johanna Pauline Taks, an Estonian immigrant with an unshakeable faith in the ability of 1940's superstar racehorse Bernborough.

Taks was a resident of Sydney's notorious College Street - once an area known to draw sailors keen for a 'good time' *nudge nudge wink wink*. She would appear at the track impeccably attired in her elegant black dresses, and first backed Bernborough in December of 1945, when the mighty ‘Toowoomba Tornado' contested the Villiers Stakes at Randwick.

The huge-striding six-year-old won both the race and Taks' heart, with the besotted woman raking in the cash as she successfully backed Bernborough in another 14 consecutive races. Even the popular press latched onto the story, with the Woman In Black attracted a huge following in the betting ring whenever she appeared on course.

But like so many punters over the years, the 'Plungeress' went to the well once too often.

On Caulfield Cup Day 1946, the 7/4 Bernborough trotted onto the track burdened with a crushing 68kg, whilst the Woman In Black trotted into the betting ring burdened with piles of cash.

Estimates of the exact figure of her wager range as high as an astronimical £310,000 from one enthusiastic source, though £6,500 seems the most accurate (still enough to purchase a majestic harbourside home at the time).

So just as she had 15 times prior, The Woman In Black went 'Bang!' and dropped the lot on Bernborough to win.

In one of what must have been the most painful ‘watches' of all time, Taks was subjected to a good old fashioned horror show as Bernborough copped a ton of interference and failed to unleash his monster finish, only managing to stagger into fifth.

For her part, a stunned Taks staggered from the racetrack never to return, but not before optimistically telling reporters that she was "not a reckless punter". Orly?

Final wash-up: Punter bust; never seen on track again.

Punter #2: “The Bag Lady”

The Bag Lady would turn up on course with a bodyguard (Detective Senior Constable Mick Hosi) - her face concealed under her trademark black veil - and back the first favourite to win $14,000.

If the fave got up, she'd head home with her loot. If it got rolled, she'd back the second favourite to get her initial loss back, as well as secure her $14,000 profit. Greyhound scribe Jeff Collerson told dogs.com.au that there was some method to the Bag Lady's madness...

"She had studied statistics and no race meeting at Wentworth Park had been held for years without at least one favourite winning."

The stakes got incredibly high some nights when several favourites would go under consecutively, but the Bag Lady held her nerve.

"One night she backed a dog called True Blue Tah, only an average 5th grader. She put $220,000 on the dog - which at the time was the biggest bet ever on a greyhound race - to get her losses back and make $14,000. It won."

Known only as 'Val', the Bag Lady had arranged a line of credit with bookmakers Kevin Duffy and John Stollery, though she did have $100,000 delivered to the track each night in a Brambles armoured truck to convince the bagmen she was 'good for it'.

"Val started off as a small punter and has just kept winning. She has been very lucky," her minder Detective Hosi told the Sydney Morning Herald in 1989.

A few favourites were 'got at' (including a dog named Cee Me Ezy, who drifted from 7/4-on to 5/2 before running appallingly), but this fearless punter still managed to continue her hot streak of getting at least one favourite home to secure her $14,000 profit.

Finally however, things came a-cropper for the Bag Lady when the law of averages caught up with her and she lost it all one fateful night at Wenty. As Collerson recalls:

"Every favourite lost, John Stollery made a stack, and the bag lady was never seen again. I can remember John saying to me when he decided to take her on that 'eventually one of us is going to go broke'. In the end it was the bag lady."

Final wash-up: Punter bust; never seen on track again.

Punter #3: “Louis The Possum”

The market gardener turned up at Randwick one day in 1906 and wagered £50 on a three-year-old called Poseidon, whose name he would pronounce 'Possumum'. The 3/1 Poseidon saluted, so securing for all time the affections of Jimmy Ah Poon - or 'Louis the Possum' as the bookies used to call him. Jimmy was hooked, and resolved to back 'Possumum' whenever possible.

In an incredible season, Poseidon (above) took virtually all before him, getting the money in 11 of his 14 starts. His wins included the AJC Derby (at the juicy odds of 7/1, which Jimmy didn't hesitate to snap-up), the Caulfield Cup, the Victoria Derby and the Melbourne Cup.

Amazingly, Jimmy rolled his ever-building bank over onto Poseidon in every one of his wins, but something intuitively told him not to back the champion colt in his three defeats.

And unlike the Woman in Black and the Bag Lady, Jimmy Ah Poon knew when to quit...

Having collected a total of £35,000 due to his continued support of 'Possumum' (valued today at £2,975,376.34!), Jimmy jumped on the first ship back to his homeland to live a life of luxury.

Final wash-up: Bookie bust; punter never seen on track again (last seen having a froffie getting on a boat to China with wheelbarrows full of cash).

Have you ever ‘let it ride' with spectacular consequences? Share any big parlay wins (or fails)...