He was from the eleventh crop of foals sired by Stay Gold a horse whose wins included the Dubai Sheema Classic and Hong Kong Vase in 2001.

After being settled towards the rear by Matsuoka he was switched to the outside in the straight and produced a sustained run to take the lead in last 100 metres and win by half a length from Outliers.

In the Shuka Sho over 2000 metres at the same track he started slowly, and never looked likely to win despite making late progress on the outside, coming home eighth of the eighteen runners behind Al Ain.

[7] Win Bright was then stepped up in distance to contest the 2400 Tokyo Yushun on 28 May, in which he started a 133/1 outsider and finished towards the rear behind Rey de Oro after fading in the closing stages.

[8] After a break of over four months Win Bright was matched against older horses in the Grade 2 Mainichi Okan over 1800 metres at Tokyo and finished tenth of the twelve runners behind Real Steel.

He returned to the track in autumn but failed to reproduce his best form in two races, finishing tenth to Logi Cry in the Fuji Stakes at Tokyo in October, and ninth to Stelvio in the Mile Championship at Kyoto Racecourse in November.

As in the previous year, Win Bright began his season in the Nakayama Kimpai and went one better than in 2018 as came with a strong late run on the outside to take the lead inside the last 100 metres and won by half a length from Stay Foolish at odds of 7.4/1.

[11] In the following month he started at odds of 6/1 as he attempted to repeat his 2018 success in the Nakayama Kinen, facing ten rivals including Deirdre, Lucky Lilac, Epoca d'Oro, Stelvio and Suave Richard.

After starting slowly Win Bright settled in mid-division on the inside as Time Warp set the pace from Glorious Forever, before making a forward move on the final turn.

He briefly struggled to obtain a clear run in the straight but overtook Pakistan Star 100 metres from the finish and won by three quarters of a length from Exultant and Lys Gracieux.

[13] Matsuoka, who was recording his first Grade 1 win in ten years, commented "We didn't get off to a good start but we still managed to travel in the position we wanted to and everything worked out in the end.

[18] Win Bright returned to competition in the autumn edition of the Tenno Sho at Tokyo on 1 November when he started a 180/1 outsider and came home tenth of the twelve runners behind Almond Eye.