How to play the gambling game and win

The tricky bit about gambling is being subject to wild swings of fortune. Even with my modest level of staking, I can easily lose £1,000 a month five months on the trot, and then, come June, have a wildly successful time betting on Wimbledon and get back not just the £5,000 I've lost so far but another £5,000 on top.

This presents a problem when trying to outperform the FTSE All-Share. In just a month I could outperform the index by several hundred per cent or, more likely, the index could put me to shame and make a mockery of this alternative mode of investment.

I tend to bet in multiples of £50, up to £250, and stick to a staking plan of 0.5 to five points - with one point being equal to £50. I never bet more than five points.

30 April: The 2000 Guineas, Newmarket

Newmarket plays host to the 1000 and 2000 Guineas, the first two Classics of the British turf season. I really fancy a horse called Roderic O'Connor.

There is a bit of value, as he has to beat hot favourite Frankel. I place £100 on Roderic to win at 8/1, but Frankel is victorious; Roderic troops in 11th out of the 13 runners.

Later, I find value in Sole Power. He won at York last August, at a huge price of 100/1. I place £100 on him at 8/1. He finishes third.

Added to my two big losing bets, I have lost another £60 on Placepot bets (a Tote-organised 'pooled' bet where you have to find a placed horse in each of the first six races and the pool is shared between the winning tickets) and £100 on the other races on the card.

Amount invested: £360
Amount returned: Nowt
Running profit/loss: -£360

1 May: 1000 Guineas

I buy the Racing Post to see if I can spot the 1000 Guineas winner, which is run over the same course as the 2000 Guineas but is for three-year-old fillies rather than colts. I like the look of Blue Bunting at 9/1, and also Havant, so put £50 on each one to win.

Havant is nowhere, but Blue Bunting wins by three-quarters of a length, returning £500. I lose £25 on three other races on the card.

Amount invested: £175
Amount returned: £500
Running profit/loss: -£35

7 May: Ascot

Last weekend at Newmarket, one of the horses that caught my eye was sprinter Hawkeyethenoo. I place £50 at 8/1 on him in the 28-runner race. He wins - lovely - and I take down some decent moolah, but the edge comes off as I lose £150 on other runners.

Amount invested: £200
Amount returned: £450
Running profit/loss: +£215

13 May: York, Newmarket and Newbury

A look at my Betfair statement says I bet on six horses on these cards, with just one winner, Hoof It, ridden by Kieren Fallon. I lost £125 on the 'meatballs', but the winner returned £181.25.

Amount invested: £150
Amount returned: £181.25
Running profit/loss: +£246.25

14 May: Lockinge Stakes at Newbury & Eurovision Song Contest

I want to take on Canford Cliffs, the hot favourite in this Group One race, with his stablemate Dick Turpin. I put £100 on Dick at 4/1, but he fails to deliver. I lose £150 on other bets on the card to boot.

I lose another £100 betting on Ireland to win the Eurovision Song Contest. Now I know why everyone hates Jedward.

Amount invested: £350
Amount returned: Zilch
Running profit/loss: -£103.75

15 May: Online poker

Bored, I play in a small tournament on the largest poker site, Pokerstars. It is only $11 to enter but there is a guaranteed prize pool of $200,000.

There are more than 20,000 players in it; I finish in the top 10% and win $75. Afterwards, I play my cash game of choice - six-handed Pot Limit Omaha. I spin the $75 up to $800. I bank $500 and lose the rest.

Amount invested:  $11 (£7)
Amount returned: $500 (£307)
Running profit/loss: +£197.25

19 May: Poker home game

I play in a crazy monthly game with some friends. It's been a big winner for me in the past two years, with 'pick-ups' of up to £4,000.

Tonight, I buy-in for £250 on perhaps the fourth hand of the night when we are playing Texas Hold'em. The action is fast and heavy, but when we finish at 3am I've made a decent £770.

Amount invested: £250
Amount returned: £770
Running profit/loss: +£717.25

21 May: Haydock and the Curragh

Two of my fancies from earlier in the month are running - Roderic O'Connor in the Irish 2000 Guineas, and Sole Power in a sprint at Haydock. I put £100 on Roderic to win, which he does at 7/2. I put £50 to win on Sole Power and he too goes in at 8/1.

I also have a £10 double on the two horses, which pays out at 39.5/1. I lose £175 on other bets but it doesn't matter as I'm well ahead on the day.

Match that, Footsie!

Amount Invested: £335
Amount Returned: £1,305
Running profit/loss: +£1,687.25

29 May: Hippodrome du Parc de Beyrouth

Don't ask, but I'm now in Beirut. At the track, there is a Pari-Mutuel, something akin to our Tote, and there seems to be plenty of action.

I go to the paddock; some of the ponies seem a bit out of condition, so if I stick to betting on the fit-looking ones it should be like shooting fish in a barrel. Having said that, I still lose 300,000 Lebanese pounds over the day.

Amount invested: 300,000 Lebanese pounds (£120)
Amount returned: Rien  

TOTAL PROFIT OVER THE MONTH: £1,567.25

Could investors have beaten Hipwell in May?

In comparison with James Hipwell's near 80% return on investment, the FTSE 100 lost 1.5% in May. Mike McCudden, head of derivatives at Interactive Investor, says: "After the lull in April, volatility returned to May's market, which gave short-term traders, spread betters and contracts for difference investors a chance for some action.

"Picking the right market and the right timing - through quality research and trading discipline - could have made them a terrific return. But the average long-only investor would have had a torrid time."