I’ve been looking over my gambling years, wishing that I had done some things, wishing I hadn’t done some things, and wondering why it is you never remember the horses that lose for you. Or at least, most of them. But you do remember those that come in – those that make a real difference to the size of your wallet. Here are my Top 5 betting moments – ever.

5. Monty’s Pass at Aintree: There has to be a Grand National moment, simply because you can lord it over everyone in the country, seeing as everybody else has a bet on the National. Mine was Monty’s Pass, which came in at a very healthy 16/1 for me. I was there at Aintree that day, a day that changed my vision of the National forever. It was my first – and only – National, and I was so sure that Monty’s Pass was going to win, I lumped on several hundred before the race. I was not alone – his trainer also bunged on about 100,000. I had confidence. I had so much that I topped up on the racecourse at 14/1 (boo) and even got the second-place horse each-way. Seeing Monty’s Pass canter home down the straight was unique – it was nothing like what you see on TV – and you hardly see a damn thing at the National when you’re there. All you can see is tarts in short skirts and boozed-up scouse lads trying to stand up without being sick. But it was worth it for Monty.

4. Varenne at Vincennes: Ah now if ever there were a deserved favourite, then Varenne was the one. An Italian trotter who destroyed almost every field he raced against, this was a beast of a horse. Naturally, Varenne went in as a massive favourite, even against the darling of the home crowd, General de Pommeau, but just seeing this horse in action was something else. Just wind it up and watch it go – all muscle and guts, this was a winner from the very start of the race. Amazing.

3. Six consecutive winners at Vincennes: Have you ever been to a trotting meeting? It’s amazing. I couldn’t believe it when I first went, but this form of horse racing is the working class meat and potatoes of French horse racing. Flat racing is for kings, Trotting is for the people. It was a cold February day, and the Prix de l’Amerique was the highlight. An annual festival of trotting, over 50,000 people were present, decked out in all colours, waving flags for their regions, representing their horses and cheering wildly. I had never been to a trotting meeting before, but I had my beloved Paris Turf newspaper with me and I studied the form as never before. The first race was hopeless, but the second provided a first winner. The third provided a 1-2 and the fourth provided yet another winner. And on, and on, and on… the Swedish guys next to me couldn’t understand how I was picking so many winners, and I assured them that it was a freak happening. Six consecutive winners at Vincennes, a feat I have never repeated, and am never likely to repeat again.

2. Everton to win the Cup in 1995: As a bluenose, I can be forgiven for believing that Everton will win the FA Cup every single year, but 1995 seemed like a very special year. The previous year we had just about cheated our way out of relegation despite having the useless Mike Walker in charge. He soon departed, after losing the first 14 games of the 94-95 season, and in came God – Joe Royle. Our form from the minute he arrived was Championship form – and it was so easy: get Hinchcliffe to take loads of corners. That’s how it worked. I knew from the minute Jackson hit the winner at Bristol City in the 3rd round that Joe Royle would win us the Cup. Before then – and ever since – I have never felt that confident. And there it was in May – Paul Rideout of all people, heading in the only goal to beat United, and Neville Southall in one of his last games for the club, keeping out the whole Utd team single-handedly. Brilliant.

1. Hurricane Run in the Prix de l’Arc de Triomphe: I will keep saying it – I bet on this race every year because I know that 9 times out of 10, I can find a winner. Hurricane Run was the three-year-old of the year, but the English punters on the course were all backing the Derby winner (as they always do). I had put my money on ante-post betting, a hundred here, a hundred there – so confident was I that Hurricane would win the Arc. And then came the start – it was already murky overhead in Paris but then the deluge began – thunder, lightning, and the skies turned black – was this an omen? A hurricane? I’ve never been at a more exciting race meeting than this – and Hurricane Run didn’t let me down, winning by some distance. One of the best three-year-olds I’ve ever seen. And definitely the most I’ve ever won on a single race. Wonderful.