Tobougg made his debut in a maiden race at York in late August. He lost ground at the start and had trouble finding a clear run, but once switched to the outside he ran on strongly to win by a length and three quarters. Despite the unimportant status of the race his performance attracted attention, with press reports calling him "a future star" and bookmakers offering him at 25/1 for the following year's 2000 Guineas. Channon called him "a lovely horse" while his jockey Craig Williams emphasised the ease of his win by claiming that "he hardly knew he had a race". Tobougg was then immediately moved up to Group One level for the Prix de la Salamandre at Longchamp, for which the leading fancies were the Prix Morny winner Bad As I Wanna Be and the Railway Stakes winner Honours List. Settled in third by Craig Williams, Tobougg was moved up to take the lead a furlong out and pulled clear to win by two lengths despite being eased down in the closing stages. Mick Channon, who watched the race on television from home after forgetting his passport called Tobougg a colt of the "highest quality" while adding that he had a "quirky temperament". After the race Tobougg's price for the Guineas contracted to 10/1, and speculation began that he would be removed from Channon's stable to join Godolphin. On his final start of the season, Tobougg was sent to Newmarket for Britain's most prestigious two-year-old race, the Dewhurst Stakes. Sent off the 7/4 favourite Tobougg raced prominently before moving into the lead two furlongs out and winning "comfortably" by one and a quarter lengths from Noverre. The Independent called it a "smooth performance" while pointing out that the field may have been below the usual standard. The bookmakers responded by cutting him to 8/1 for the Guineas. Before the end of the season, Tobougg's ownership, as had been predicted, was transferred to the Maktoum family's Godolphin Racing operation and he was moved to the stable of Saeed bin Suroor, spending the winters in Dubai before being moved back to Britain during the Summer.
2001: three-year-old season
On returning from Dubai, Tobougg was sent straight to the 2000 Guineas without running in a trial race. He was the chosen ride of Godolphin's stable jockey Frankie Dettori despite the fact that he had been beaten by his stable companion Rumpold in a private trial race in Dubai. Dettori rode the colt in all but one of his subsequent races. He was made 4/1 favourite in a field of eighteen, but after racing prominently he made little impact in the closing stages and lost his unbeaten record, finishing eighth behind Golan. The Godolphin team were unable to explain his "dismal" performance. A month later, Tobougg was moved up to a mile and a half for The Derby and ran creditably, finishing strongly to take third place behind Galileo and Golan. At Sandown in July he finished fourth as 9/4 favourite for the Eclipse Stakes, beaten less than a length behind Medicean. Dettori reported that the colt "hated" the firm ground. Tobougg was then off the course for three months before returning in the Champion Stakes at Newmarket. Ridden by Kevin Darley he tracked the leaders before moving into the lead a quarter of a mile from the finish. he ran on well but was headed inside the final furlong and beaten three quarters of a length by Nayef. On his final start of the year he traveled to Hong Kong where he faced an international field in the Hong Kong Cup. Dettori sent the colt into the lead from the start, and after being headed a furlong out, Tobougg rallied strongly but was beaten a head by the Japanese runner Agnes Digital. Saeed bin Suroor was pleased with the colt's effort and said that he would be "a serious horse next season."
2002: four-year-old season
Tobougg failed to live up to his trainer's prediction in four starts in 2002. He finished last of the fifteen runners behind Nayef in the Dubai Sheema Classic, and on his return to Europe, ran fifth behind Rebellline in the Tattersalls Gold Cup. Having run in nine consecutive Group One races, Tobougg was dropped in class for the ListedSteventon Stakes at Newbury in July. He started Evens favourite, but could finish only third to Highdown. For his final race he was sent to Belmont Park where he finished last of the eight runners in the Man O' War Stakes.
Assessment
Tobougg was named European Champion Two-Year-Old Colt at the Cartier Racing Awards in 2000. In the official International Classification for 2000, released in January 2001, Tobougg was ranked equal third on 120, behind the colts Minardi and Okawango and equal with the filly Superstar Leo. In 2001, Tobougg was rated the eleventh best three-year-old colt in Europe, with a rating of 119.