In 1889 she won the Darlington Open In 1891 Jackson competed in the singles event at the Wimbledon Championships for the first time.

In the first round she defeated Maud Shackle, but lost in the quarterfinals to Bertha Steedman in two sets.

[1][2][3] In 1894 she had defeated Cooper in the final of the South of England Championships held at the Devonshire Park Lawn Tennis Club, in Eastbourne.

That same year she also became the singles champion at the Welsh Championships in Penarth after a straight-sets win in the final against Ethel Cochrane.

Her other career highlights included winning three consecutive singles titles at the Scottish Championships between 1890 and 1892.