In the following month was moved up in class and distance for the Grade III Kisaragi Sho over 1800 metres at the same course and recorded his first major win, beating Bold Emperor and thirteen others.

On 8 November he faced King Halo, Bold Emperor, Seiun Sky and Daiwa Superior in the Grade I Kikuka Sho over 3000 metres at Kyoto Racecourse.

He was in sixth place entering the straight and made steady progress in the closing stages to finish third behind El Condor Pasa and Air Groove.

Special Week began his third season in the Grade II American Jockey Club Stakes at Nakayama on 24 January and won from Silent Hunter and Mejiro Steed.

The Grade I spring edition of the Tenno Sho over the same course and distance saw Special Week matched against eleven opponents including Mejiro Bright (winner of the race in 1998), Matikanefukukitaru, Seiun Sky, Stay Gold, Silk Justice (Arima Kinen).

In the Tenno Sho over 2000 metres at Tokyo on 31 October, Special Week attempted to become the second horse to win both the spring and autumn editions of the race in the same year.

The race attracted a seventeen-runner field including Mejiro Bright, Silent Hunter, Tsurumaru Tsuyoshi, King Halo, Seiun Sky, Stay Gold, Stinger (Hanshin Juvenile Fillies) and Air Jihad (Yasuda Kinen).

In a closely contested conclusion to the race, Special Week prevailed by a neck from Stay Gold, with Air Jihad, Stinger, Seiun Sky and the outsider Embrasser Moi all finishing within two lengths for the winner.

The other European challengers were High-Rise, Borgia and Fruits of Love (Hardwicke Stakes) whilst Hong Kong was represented by their Horse of the Year Indigenous.

[16] c = colt, f = filly Special Week was the inspiration for the main character of the media franchise Uma Musume Pretty Derby,[17][18] of which the 2018 anime premiered shortly before his death.