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. The following year, 1892, she lost in the first round (which was the quarterfinal) to Shackle. Her last entry came in 1895 when she reached the final of the All-comers' event after victories against J.M. Corder, Bernard and
Alice Pickering. She lost the final in two close sets to
Charlotte Cooper after having led both sets 5–0. 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. She lost her title in 1895 after a defeat in a three-sets final to
Jane Corder. 1895 was one of Jackson's most successful seasons she won 4 titles that year, and was joint title leader with England's
Charlotte Cooper and Canada's
Maude Delano-Osborne, but she reached the most finals that season with 8 appearances. Her other career highlights included winning three consecutive singles titles at the
Scottish Championships between 1890 and 1892. the
Northumberland Championships four times 1889 to 1891, and 1894. She won the
Yorkshire Championships three times consecutively from 1891 to 1893. In addition she also picked up two
Derbyshire Championships titles in 1892 and 1895. Her other big title wins came at the
North of England Championships in 1891, the
South of England Championships in 1894, and
West of England Championships in 1895. In 1898 she was a finalist at the
Championships of Berlin on clay where she lost to
Clara von der Schulenburg. ==Grand Slam finals==