Winkipop was foaled in 1907 at the Cliveden Stud, a Thoroughbred breeding farm owned by Waldorf Astor at his family's estate near Taplow in Buckinghamshire.

Winkie was not a successful racehorse and was exported to New Zealand as a breeding stallion, where he sired the mare Entreaty, the dam of the multiple stakes winner, Phar Lap.

[4] In the first start of her racing career, Winkipop was fifth in the Foal Plate at Lingfield Park on 10 July, running against the seasoned racehorses Yellow Slave and Greenback.

[11] At Ascot in June, Winkipop won the Coronation Stakes while carrying seven more pounds than the nine other contenders as a penalty for winning the 1,000 Guineas.

[12] She was second in the Royal Stakes held at Newbury a few weeks later, losing by three quarters of a length to Lord Villiers' colt Greenback with the future stallion Willonyx third.

[13] In the Nassau Stakes at Goodwood in July, Winkipop faced off against Mr. Nelke's filly Yellow Slave over a mile and a quarter distance.

[14] Her next engagement for the Durham County Produce Plate at Stockton was "an affair that [could] scarcely be called a race" where Winkipop won by two lengths and conceded 24 pounds to her opponents.

Her most notable offspring include the mare Plymstock who produced the 1929 Oaks winner Pennycomequick by Hurry On and the colt Blink which won the Princess of Wales's Stakes and was second in the Derby.

[24] Salmon had made his fortune in the New York real estate market and leased a 600-acre farm called the Mereworth Stud in Lexington, Kentucky.