Tony McCoy has won a Grand National, the Gold Cup twice and the Champion Hurdle three times. In April 2002, his 270th winner of the season beat a record that had stood, apparently impregnable, for 55 years. For more than a dozen years, since McCoy passed Richard Dunwoody’s career total of 1,699 winners, every success has moved the all-time mark further forward, and reduced the already remote chance that his lifetime record will ever be approached, never mind surpassed.

Yet McCoy has never tamed Cheltenham’s Festival meeting. He has dominated every other week of the jumps season for the last two decades, but only rarely has he finished at the front of the pack in the week that matters most of all. In 1997, in just his second season as a senior rider, McCoy was the Festival’s leading jockey with three winners. A year later, he equalled what was then the record for the meeting with five winners, and was the Festival’s top rider for the second time. The second, and also the last.

It is, on the face of it, a perplexing Festival record. Even in the recent, four-day era, which started halfway through McCoy’s career in 2005, he has ridden three winners at the meeting only once, in 2006, when Ruby Walsh took the riding title with the same winning total but more second-place finishes. In all, there are 23 races at the Festival open to senior riders. In the last five seasons, McCoy’s total of winners for the week has been: two, two, two, two and one.

Yet these are numbers that say much more about the intensely competitive nature of the Festival than any fragility in a jockey who has ridden nearly 4,500 winners over the last two decades. This is a meeting where Jonjo O’Neill once finished as the leading jockey with a single winner. At seven of the last 13 Festivals, no jockey has ridden more than three winners.

On that basis, McCoy’s five winners from 17 available races in 1998 could be seen as almost a match for Ruby Walsh’s remarkable seven victories from 22 events open to senior professionals in 2009 (no one else, incidentally, has even reached six victories at a single Festival). Neither record, though, is quite a match for Jamie Osborne, who rode five from 15, a third of all the races open to senior jockeys, in 1992.

“I got off the winner of the Triumph Hurdle [Duke Of Monmouth] that year too to ride something else so it could have been even better,” Osborne said on Monday, “but there you go. It was probably a fluke.

“I think with regard to Tony McCoy’s record at the Festival, it’s just one of those little freaks of probability. Realistically, he’s not riding necessarily for the most successful Festival trainers. When you think about the domination of Willie [Mullins] and Ruby [Mullins’s stable jockey], he’s coincided with that era, and I suppose Nicky Henderson has provided plenty for Barry [Geraghty], and there’s really nobody else who’s won it [in recent seasons].

“In the past, Ruby has had the best of Willie’s and Paul Nicholls to choose from, and if you’re not on those quality horses, you’re not going to beat them. I certainly don’t think there’s any flaw in the McCoy armour. Yes, everybody needs a little bit of luck there, but it’s a lot easier when you’re on the best horse. If you were to look at the average price of his rides, he’s probably done well to win it twice.”

It is a crucial point, but one that can be overlooked, even by the jockeys themselves. There are both physical and physiological limits on the fastest time that any horse can run from A to B. A jockey can only help a horse to approach its best time as closely as possible in any given race, and at the Festival above all, even its very best will often not be good enough.

“One thing that used to almost amuse me a little bit is that it’s the same bunch of horses you’ve been riding against all year, but some riders seemed to feel that because it was the Festival, their horses could go faster than they’d been going all season,” Osborne says. “Sometimes jockeys could make errors, in judgement of pace mainly, and the occasion would get to some riders more than others. The more practice you get riding big horses in big races, the better your judgement, and the less fazed you are by it.

“I don’t think anyone could point that finger at McCoy, but there are a few over the years that you could. It’s hard not to get drawn into going too fast sometimes, because you think they can’t all be wrong, but they can. Someone like Charlie Swan was always brilliant at that, he didn’t give a shit and would always back his own judgment. But you’re talking about small margins of judgement that only people doing it regularly can really understand. From the grandstand, it will always be very difficult to pick up.”

Swan, the Festival’s top jockey in 1993 and 1994, also sees nothing strange in McCoy’s failure to win the meeting’s riders’ title since 1998.

“You need so much luck and you need your main stables to have a good few winners,” Swan says. “It’s so competitive and there so many runners, it’s quite tight around there and all the best horses are going there. When I won it, I think they were all for different trainers. If you’re first jockey to Jonjo O’Neill and [leading owner] JP [McManus, who retains McCoy], it’s not so easy to get on the good outside rides.

“I would probably have had only three or four rides for my retaining stable, but I was getting the best rides from the other Irish horses coming over. It’s a bit easier when that happens. When Ruby doesn’t have a ride for Willie Mullins in one of the handicaps, he’ll often get on one of Tony Martin’s, and he’s one of the best trainers of handicap horses. That’s a chance of another winner or two.”

Walsh is odds-on with the bookmakers to finish this week’s Festival meeting as the leading jockey for the eighth time in the last 10 years. He has 41 winners at the meeting already, 11 ahead of McCoy and 10 clear of Geraghty, whose Festival career should continue for a year or two yet.

McCoy, meanwhile, is 14-1 to go out on a high as the week’s top jockey, and has only one likely favourite in his book of rides. Even that owes as much to sentiment as form, since Ned Buntline is McCoy’s probable ride in the Grand Annual Chase, the final race of the week, which has been renamed in his honour this year to mark his impending retirement.

McCoy conceded on Monday that he will be “sad” to leave the Festival weighing room for the final time “because Cheltenham will be different for the rest of my life”. Osborne wonders whether the most successful jump jockey of all time will return a spectator, in the early years of his retirement from the saddle at least.

“I didn’t go back for a few years after I gave up,” Osborne says. “Now, I can go as a spectator and enjoy it, but he might struggle to begin with. What you don’t quite realise is that you become almost subconsciously addicted to the adrenalin. If you’re injured, you don’t feel it because you’re working hard to get back, but when it’s actually over, everybody goes through it. It’s like a chemical imbalance for a while. It takes time to lose that daily fix of adrenalin.”