After 30 wildly successful years at the Ballydoyle helm, milestone moments are coming like buses for Aidan O’Brien, although even by his own stellar standards the prospect of reaching a century of Royal Ascot winner this week constitutes a notable landmark.The Irishman, who has rewritten European racing’s record book, stands on 96 career winners at British racing’s world-famous showpiece occasion. Since he has averaged five winners a week for the last four years at Ascot the odds are a once almost inconceivable 100 is on the cards. Another handful of winners this week will also put him firmly to the forefront of the race for the prestigious leading trainers award again. O’Brien has already won it 13 times. Arriving at the summer extravaganza on a run of seven classic victories in six weeks means Ballydoyle momentum seems almost irresistible. Since the racing world really does zero in on the upcoming five days in Berkshire, it ensures that the 56-year-old Irish maestro will be a focal point of attention despite all the regally infused pomp that makes Royal Ascot so unique. Ever since his first success at the meeting – with Harbour Master in the 1997 Coventry Stakes – O’Brien has consistently delivered on the week that matters most, a major element in the longevity of his relationship with his Coolmore bosses.It’s a decade since he delivered seven wins in a single Royal Ascot, a feat matched only by the great Henry Cecil. He is well clear of his nearest competition, John Gosden (71 winners), with the scale of the achievement underlined by his nearest current Irish rival being Dermot Weld on 18.O’Brien’s closest domestic competition is increasingly his son Joseph, who is attacking this Ascot in numerical force too. The 33-year-old pitches 10 runners into Tuesday action including seven of the Irish hopes in the marathon Ascot Stakes over two-and-a-half miles.Trainer Aidan O'Brien at Ascot Racecourse, Berkshire, on June 21st, 2023. Photograph: David Davies/PA Wire That’s the race where racing royalty teams up with the real thing as Willie Mullins saddles Reaching High, owned by King Charles and Queen Camilla. The horse finished out of the money in the same race a year ago.Mullins has a dozen Royal Ascot victories of his own, proof that jump racing’s dominant figure has the capacity to successfully cross the codes long before Ethical Diamond’s Breeders Cup victory last November.However, there is some fresh blood to this week’s Irish challenge which comes to almost 30 runners on Tuesday. [ Siobhán Rutledge named sportswoman of the month for MayOpens in new window ]Co Meath-based Mick Mulvany breaks new ground with a pair of runners in the big two-year-old contest, the Coventry Stakes. Jockey Wesley Joyce, who almost lost his life in a fall at the Galway festival four years ago, has opted to ride Listowel winner The Scallionator. But as has mostly been the case for three decades, the bulk of quality at a meeting where it counts more than anywhere else will be with O’Brien snr. He recently reacted with little fuss to reaching 50 English classics with Christmas Day winning the Epsom Derby; reaching 100 at Royal Ascot is unlikely to make for a different response.“He’ll reach 100 and it won’t make a blind bit of difference to Aidan,” his former number one jockey Kieren Fallon said. “He will just roll on, keep doing the same thing and be back again with probably a better team next year. He’s a genius of a trainer.”It’s Ryan Moore who has had the happy task of steering home more than half of O’Brien’s Royal Ascot winners. The English jockey, who won Sunday’s French Oaks on Diamond Necklace, has a shot at his own century this week. Currently on a record 92 Royal Ascot winners, the 42-year-old rider has been top jockey at the meeting 12 times. In 2015 he enjoyed the best week ever enjoyed by anyone when booting home nine winners.Two years before that Moore landed the Gold Cup on the royal runner Estimate. He will carry the same silks on board Reaching High although his prime Day One focus is likely to be Gstaad in the St James’s Palace Stakes.Coolmore’s stallion making business underpins so much of the Ballydoyle operation and there are few more commercially important races than the St James’s Palace over Ascot’s round mile. Ryan Lee Moore on Gstaad wins the Tattersalls Irish 2,000 Guineas on May 23rd, 2026. Photograph: Laszlo Geczo/©INPHO Gstaad has almost three lengths to make up on Bow Echo from Newmarket’s 2,000 Guineas last month and despite subsequently scoring himself in the Irish Guineas there appears little reasonable logic to assume he can bridge the gap. But that’s without reckoning on his trainer at Royal Ascot, something his son realises better than most. “It would be extraordinary for him to get to 100 – it is hard enough to have one winner at Royal Ascot, it’s the toughest meeting in the world to have winners at,” Joseph O’Brien said. “Every year, dad and Coolmore go there with a strong team. But it would still be a magnificent feat.”