Privately purchased in 2020 in conjunction with Mandore Agency, Crystal Cliffs picked up her first stakes win with a 2 3/4 length success in the Sand Springs Stakes at Gulfstream Park. This success came after finishing 2nd in the G3 Regret at 3 and 3rd in the G3 Eatontown at 4.

Crystal Cliffs became a graded stakes winner when shipping north to Woodbine and taking the G2 Nassau in a dead-heat with G1W Lady Speightspeare.