[1][2] Pretty Gorgeous is owned in partnership by O'Brien's mother Anne-Marie and John Oxley racing in alternating colours.

Pretty Gorgeous made her racecourse debut in a maiden race over one mile at Bellewstown on 2 July when she was ridden by Shane Crosse and went off at odds of 2/1 in nine-runner field.

She started favourite but despite making strong progress in the last quarter mile she was beaten into second place by the 14/1 outsider Shale (trained by Joseph O'Brien's brother Donnacha).

[10] On 9 October Pretty Gorgeous was reunited with Crosse when she was sent to England and moved up in distance for the Fillies' Mile at Newmarket Racecourse.

The filly had been scheduled to run in the Prix Marcel Boussac a week earlier but the O'Brien contingent was withdrawn en masse when four horses failed drug tests, with the results being attributed to a batch of contaminated feed.

After racing in mid-division she moved up to challenge the front-running Dubai Fountain in the last quarter mile, gained the advantage inside the final furlong and held on to win by half a length from Indigo Girl with the same distance back to "Snowfall" in third.

[15] In the official European classification of for 2020 Pretty Gorgeous was given a rating of 113, making her the equal best two-year-old filly of the season alongside Campanelle and Shale.