Simon was born on 14 July 1966, in Axminster, Suffolk, and, as an unknown amateur, rode out for a couple of point-to-point trainers.
Among the horses he worked with was Just So, trained by Julie Barrow.
Their first race together came at the now-defunct venue of Nedge at Telford. Just So ran out.
Then Julie entered the horse at Williton, Taunton, where he finished third.
The intrepid pair then came second at Kingston St Mary, Taunton, before winning their first race together at Holnicote, Exmoor.
Just So was owned and bred by Henry Cole. After the horse had won a further two point-to-points during the 1989 season, Cole decided that it was time to step up the horse's sights. He lodged Just So with Taunton trainer John Roberts who, in January, 1990, entered it into a novice chase at Chepstow. Ridden by Simon, Just So won easily so was entered in the Wincanton Gold Cup. Here they finished fourth but, with Garrison Savannah the winner, it was a good result.
Simon and Just So then moved on to the National Hunt Chase at Cheltenham. They finished twelfth behind Topsham Bay.
Simon rode 11 winners as an amateur.
On November 20, Simon turned professional and, in 1992, Just So had his first stab at the National. Unfortunately, Just So ran best on soft going: that year it came up good to soft and, in the circumstances, he did well to finish sixth.
It was too firm for Just So to compete the following year but he and Simon were back again in 1994 when incessant rain had provided the perfect going for them.
Simon was obliged to put up three pounds overweight and, carrying ten stone three, failed by just one and a quarter lengths to beat Minnehoma.
The three pounds overweight had been the difference between victory and defeat and Simon acknowledged this.
'I couldn't do any lighter' he admitted after. 'I'm just grateful that the owner stood by me.'
Simon picked up a four-day whip ban, having finished second on Just So. (Jan 4, 1994). The horse, which bruised easily, returned marked and the Stewards ruled that Simon had used the stick forcefully, knowing he was likely to injure the horse.
Simon was given second whip ban, this time for 10 days, when once again marking Just So in the process of the pair winning the John Hughes Trial Handicap at Chepstow. (Sat. 7 Feb 1994).
He appealed against this decision but lost.
'I was only trying to do the job I'm paid to do' he said after the hearing.
When aged 27, with no big stable to rely on, Simon found life a constant battle for rides and recognition.
Even when he had finished runner-up in the Grand National, scarcely a mention was made of him in the press.
With only eight winners behind him for the season up to that point (April 1994) he said; 'Just because my name's not Adrian Maguire or Richard Dunwoody, I don't seem to get the publicity. It's the way my career has gone. You just have to struggle on week after week, hoping to get a break. There's no point in getting down about it. I feel I've done quite well with the horses I've ridden. I could do with one or two more good ones, that's all.'
Having had his final rides at Exeter on January 27, 2003, Simon eventually turned to training and achieved his first double when Eluvaparty and Deep Quest both scored at Exeter (November 13, 2007).
