My old idea was based on the Martingale system – sometimes used by unwise roulette players – which involves doubling your stake every time you lose so that when eventually you win, you recoup all your losses plus a profit equal to your original stake. Its obvious flaw is that the exponential nature of the maths means that you are soon placing very large bets. Say your initial stake is as small as £10. After only seven losses you will be placing a bet of £1,280. If you lose again – and of course your chances of winning at any point are not improved by the fact that you have already lost many times – the next bet will be £2,560. Lose again and it will be £5,120. A sequence of ten losers will wipe out a £20,000 starting bank – if you can even find a bookie to take your final £10,240 bet – and all in an attempt to win a single tenner. It is not a practical way of making money.

What I set myself to do, therefore, was somehow to adapt the Martingale system to make it more robust against improbably long sequences of losses. Any Martingale system is likely to tick over happily for quite a long time before it hits the statistical freak that wipes it out. This illusion of effective operation is compelling; it makes the problem – the brute mathematics of the inevitable iceberg – seem like a flaw that can somehow be fine-tuned away. I spent a lot of time, in the late summer of 2004, trying to do just that. Then, as with so many things, I found that someone else had already done it, a man by the name of Barry Hughes, who had developed something he called the Retirement Staking Plan. What his plan did was divide a large loss into a number of smaller ones and then retrieve them one by one. This kept the stakes within manageable limits, and the Retirement Staking Plan was able, said Barry, to survive sequences of up to forty-eight losses.

I tested it using the selections of a former jockey who had an online tipping service to which I had subscribed, and it seemed to work. That is, it made money over time and survived – sometimes only just – long sequences of losses. Excited by its success, to penny stakes at first, I started to operate it live. (I should say at this point that I had absolutely no interest in horse racing per se whatsoever. The names of the horses that the tipster put up meant nothing to me.)

Barry’s staking plan and the jockey’s selections produced money smoothly throughout the autumn. I say smoothly – no doubt there were stressful moments, especially as I stepped up the stakes. Fairly soon I was putting on individual bets of several hundred pounds. With somewhere between ten and twenty bets a week, a nasty sequence of losses might be put together in only a few days, and even with Barry’s supposedly fail-safe plan there was a sense, especially at first, of never being far from snowballing disaster. Still, there had been sequences that would have sunk a simple Martingale system that Barry’s maths had successfully negotiated. Money was being won – and money won, so the saying has it, is twice as sweet as money earned. There was one day that sticks in my mind, when I won over £5,000 – I was in London at the time and I remember emerging from the Tate Gallery late in the afternoon and wandering into the nearest William Hill to find that every single one of the tipster’s four or five selections that day had gone in. That was just before Christmas.

I had in fact won upwards of £15,000 since September, and had taken to travelling first class on the Eurostar when I went back and forth between Brussels and London, preparing for the relocation that was due to happen at the end of January. I fully believed that I had solved my income problem, and spent a fair amount of time shopping for expensive wine. What happened next was heartbreaking. It wasn’t like a hydrogen bomb – the exponential catastrophe of the typical Martingale system. Barry’s plan ensured that it was slower and less dramatic than that, and perhaps more painful as a result. For most of the two winless weeks, I was staking £500 on each selection and losing more than £1000 a day. There was something unreal about it. ‘Could it really be,’ I must have asked myself, on more than one evening, ‘that I lost two and a half grand on the horses today?’ Only a few months before the scenario would have seemed outlandish, the stuff of melodrama or morality tale. When the losses reached the point where they amounted to more or less exactly what I had won since September, I stopped. I told myself that if I had not won, I had not lost either. I had come out even. Unfortunately that wasn’t the end of it.

I still had an income problem and by now had moved back to London. As it happened, I had sold my flat and was living in expensive rented accommodation – I had signed the lease in December when I thought I would be making five grand a month tax-free. I suppose it was the months of plenty before the catastrophe that persuaded me, even then, that it must be possible to make a living from betting on horses – that, and a stubbornness that made it hard for me to admit that any task I had set myself was impossible; and no doubt an aversion to plain honest work as well. The trauma of those terrible weeks in January did not, in any case, dissuade me from trying again.

I blamed the ex-jockey whose tips I had been using. He was clearly rubbish. No amount of lipstick, in the form of Barry’s staking plan, would prettify that particular pig. Having said that, I had become sceptical about the ability of any sort of staking plan to deliver reliable returns in the absence of sound selections. Selection – and this should perhaps have been obvious from the start – was the important thing. I still knew next to nothing about horse racing myself, so clearly it wouldn’t be me making those selections. I had, however, started to research the various tipsters who sold their information on the internet, and the one that intrigued me was Henry Rix. He had been in business for years and his service had a serious, professional aura. It promised only a few tips a week – the website featured a lecture on the importance of discipline. It was also reassuringly expensive – about £1500 for a year’s subscription.

Now I wasn’t about to pay that myself, no matter how persuasive a website he might have, and it’s possible that the whole thing would have ended then, were it not for my discovery of Goldline. Goldline was a so-called relay service – it would pass on the tips of the likes of Henry Rix for a much lower annual fee. When I say much lower, I mean maybe £100, rather than £1500. I can’t remember the exact figure, but whatever it was, I was prepared to pay it for access to Rix’s selections, and I immediately started to back them to £100 a point.

The important thing enabling this development was that I was already in the habit of betting hundreds of pounds at a time on a single horse. That had, since the previous autumn, become normal for me. It was something I was able to do with perilous equanimity. Goldline also relayed various other services. In addition to Henry Rix, I shelled out for a subscription to Race-Call, which came highly recommended by Dave at Goldline, and started backing their selections in late January. April saw the addition of the Sports Betting Hotline, which supplied tips on various sporting events. Finally, in June I subscribed to Golf Insider, about which Dave had been consistently raving, and started to bet on the golf too.

When I look at the spreadsheets now, that year seems like a sort of heroic age of heavy hitting. There was certainly a heroic scale to the whole thing. In late May, I won £2,400 when a horse called Celtic Mill won at Sandown. I won £2,575 when Pastoral Pursuits took the July Cup at Newmarket. Later in the same month, I won several thousand pounds when Tiger Woods won the Open at St Andrews. The extraordinary thing is, I have no memory of any of these wins. What, I wonder now, must the texture of my life have been like then, that winning those sort of sums failed to leave even the slightest mark on my memory? The spreadsheets tell of shuddering losses too, of course – over five thousand pounds lost in a few short weeks in June, for instance. Overall, though, I was making a profit. It steadily increased through the spring and early summer, took that knock in June, and then started upward again in July and August.

Although I remember nothing about the flat racing season, which started in the spring – not even the major wins and losses – I do remember bits and pieces of the jumps season, which ended in April. I remember the death of Best Mate, the multiple Gold Cup winner – he collapsed and died of a heart attack at Exeter racecourse in front of a stand full of people, a shocking incident. (That evening in the pub I told a friend that Best Mate had died that day – she thought I meant my best mate and reacted with an all-out horror that made me believe, for a moment, she was a major aficionado of the turf.) I remember the race in which Kauto Star, still unknown and having only his second run in this country, fell at the second last fence, also at Exeter as it happens, when leading. He was then remounted by Ruby Walsh and, like something out of an equine Chariots of Fire, only just failed to win the race anyway. I remember the 2005 Cheltenham Festival – the first time I had taken any interest in the event, or even been aware of it. I also remember the Grand National meeting at Aintree in April, but nothing after that, though the tipsters continued to make money through the summer.

Then, in September, they started to lose. Hull’s failure to beat Bradford, even at +18 on the handicap, in a rugby league match on which I had wagered £800, was the first sign that something was amiss. After that nothing seemed to go right. At the end of September I tried shuffling my tipsters – dropping some, introducing new ones. It didn’t work. A few significant wins in early October were enough to make me hope that the situation might be saved but November was disastrous, and by mid-December I was again facing the decision I had faced eleven months earlier – I had lost all my winnings, and had to make up my mind whether to continue, or not.

I did not continue – not then. The following year, though, I had another try, using a slightly different line-up of tipsters, and applying various statistical ‘filters’ to their selections. This time things went worse than the previous two efforts, in that rather than winning a load of money and then losing it, I just lost a load of money. Maybe five grand. I needed that. It was what I needed to persuade me to stop.

And what was left then, after two years of winning and losing hundreds, quite often thousands, of pounds a week? An affection for horse racing – for the jumps anyway, the ‘winter game’. I do love the way it takes place on truncated afternoons at unglamorous spots in Somerset and Northumberland and the Welsh borders. The mud-flecked aesthetic of it, the way it is embedded in the English landscape. I think of the sheep on the hills around Sedgefield. The shadows of leafless trees, the wind-buffeted daffodils at Plumpton on a sunny February afternoon. I prefer the so-called ‘gaff’ tracks like Plumpton, hidden away in the Sussex countryside, to the metropolitan parkland courses with their escalators and hospitality suites like airport lounges. This is a sport of farmers. I like the way the season ends in spring, like a fertility rite, as the land comes to life.

Photography by Corinne Cavallo