Better Than Ever, Gingerbread Man, Super Easy and Stepitup achieved it from 2010 to 2013 respectively.
And now War Affair looks destined to complete the Grand Slam of the Singapore-Three-Year-Old Challenge after he once again annihilated his rivals in the $350,000 Group 2 Singapore Three-Year-Old Classic over 1,400m in Race 9 at Kranji yesterday.
Three weeks ago, the Alwin Tan-trained star blitzed rivals of his own age by one and a half lengths in the $250,000 Group 3 Singapore Three-Year-Old Sprint over 1,200m in a sizzling 1min 08.86sec.
The way he won the first two legs of the series and to run against the same horses again, you don't have to be a racing expert to predict what the outcome will be in the final leg on May 16.
Yes, winning the $500,000 Group 1 Singapore Guineas over 1,600m, a distance which suits him to a T but out of reach for most of his rivals, is more or less a foregone conclusion, barring unforeseen circumstances, of course.
War Affair was crowned Champion Juvenile of last season, when he was then trained by Mark Walker.
His new trainer was almost speechless and out of breath from the excitement after yesterday's race.
"I can't think of a word to describe him any more, you know. Every time he gave us a big surprise and today he broke his own timing again," said Tan, composing himself.
"When he came to our stable, we just felt very proud of him and I also feel very proud of him, you know, that he has produced such a good result."
It was War Affair's second win over 1,400m, his first on Sept 22 last year in 1:23.10 with his former regular rider, Joao "Magic" Moreira, astride.
With new partner Danny Beasley aboard yesterday, War Affair won a long way from home in 1:21.39.
Overall, it was his eighth win from 11 starts and he has brought his earnings to $970,000.
War Affair was one of the first to jump, but Beasley allowed Straightothepoint, Lucky Mission and last-start winner Marseille Roulette to dispute the lead. He just sat behind, nice and relaxed, and bided his time.
Straightothepoint strode ahead from the 1,100m and built up a four-length lead. War Affair was fifth but just about four lengths away.
Lucky Mission, Faaltless and Marseilles Roulette closed in on the tiring leader on straightening.
War Affair loomed up menacingly on the outside and hit the front at the 300m mark.
Although he laid inwards, he began to clear away. Only one horse came charging up to challenge but Goodman could only finish two lengths behind at the winning post.
Room For Excuse dropped in third, three and a quarter lengths away.
This article was published on April 21 in The New Paper.
Get The New Paper for more stories.