When Take called in to tell Masahiro Sakaguchi, King Halo's trainer, that he couldn't make the race, Fukunaga just so happened to be present, and was asked if he could ride the horse, to which he accepted.

The horse would become the favored at the Radio Tampa Hai Sansai Stakes, but finished second after Lord Ax passed him on the final stretch.

The horse was the most favored here as well, but couldn't catch runner Seiun Sky or Kisaragi Sho winner Special Week, finishing third with a four-length gap behind the two.

At the following Tōkyō Yūshun, King Halo took the lead and ran, but as the race became the second fastest pace at the time, the horse lost momentum at the final stretch, finishing at an unimpressive 14th place.

King Halo won two group races in a row in the 1999 season, the Tokyo Shimbun Hai and Nakayama Kinen, with Yoshitomi Shibata as his new jockey.

For the next Takamatsunomiya Kinen, the horse returned to Shibata, who won the race from the outside passing the likes of Agnes World and Black Hawk at the very last moment.

In a twist of irony, King Halo's original jockey, Fukunaga, was riding the second-place horse, Divine Light [ja].

In autumn, Shibata once again rode King Halo, but did not make an impressive showing with him finishing 7th on both the Sprinters Stakes and the Mile Championship.

Later on that same year, Kawakami Princess [ja] won the Yushun Himba, becoming the first King Halo crop to win a GI race.

The horse then went on to win the Shūka Sho undefeated, and went on to finish first the Queen Elizabeth II Cup before being dropped to 12th due to interference.