The son of a West Country bookmaker, Pipe was an amateur jockey before turning his attention to training in 1974 at Nicholashayne, Somerset, near Wellington, England, at Pond House stables.
He made multiple simple but effective changes to what had been then the traditional methods of training racehorses, specifically those in jump racing.
Pipe was appointed a Commander of the Order of the British Empire (CBE) in the 2000 New Year Honours for services to horse racing.
[6] Before the race, Pipe's bookmaker father announced “I intend to lay the horse to any punters who want to back it with me.
[6] The first clue to the upward trajectory that his career would subsequently take came with the 66/1 victory of Baron Blakeney over red-hot favourite Broadsword in the 1981 Triumph Hurdle at Cheltenham.
ITV did an edition of The Cook Report in 1991 that according to the Racing Post "basically accused Pipe of every dodgy practice short of witchcraft"[9] and according to The Guardian in 2006 was "a very spiteful programme without foundation".
[6] The Times, writing in 2020, called it a "savaging" and said of the insinuations of ethical violations and cruelty, "The truth, though, was that Pipe was just getting his horses fitter than anyone else, knew precisely when they were healthy enough to do themselves justice, and ran them in the right races.
[9][17] In 2002, suspicions raised again by his successes, the Jockey Club made a "dramatic dawn raid" on Pond House and collected blood samples, all of which tested negative.
[5] Pipe went on to be Champion Trainer 15 times with successive stable jockeys Lungo, Peter Scudamore, Richard Dunwoody, David Bridgwater and Tony McCoy.
Pipe was also associated with multiple notable racehorse owners, including David Johnson, Paul Green, Freddie Starr, Terry Neill, Brian Kilpatrick, Darren Mercer, John Brown,[16] and Stanley Clarke.
Notable horses Pipe trained include Carvill's Hill, Deano's Beeno, Cyfor Malta, Rushing Wild, Gloria Victis, Pridwell, Tiutchev, Beau Ranger, Granville Again, Make A Stand, Challenger du Luc, Lady Cricket, Balasani, Cyborgo, Miinehoma, Bonanza Boy, Run For Free, Riverside Boy, Take Control, Tiutchev,[20] Omerta,[21][16] Well Chief, Cyborgo, Horsa La Loi III, Puntal, and Viking Flagship.
[22] In 1991 Carvill's Hill, owned by Paul Green and under Scudamore, "demolished" the National, carrying top weight and finishing 20 lengths ahead going away in soft, heavy going.
While other trainers fed richer diets, he weighed his horses regularly and kept them leaner during racing seasons, reasoning that "you don't see fat athletes".
[7][27][15][8] The Racing Post called him "one of the greatest trainers ever", his stables, Pond House, "legendary", and in 2023 said he had "revolutionised a profession he entered without experience, then conquered.
[6] In 2020, The Times credited him with professionalising National Hunt Racing and called his training methods the "blueprint that others now aspire to".