Gregory made her county debut in 2018, for Surrey against Worcestershire.[3] She was Surrey's leading wicket-taker in her first Twenty20 Cup season, taking 7 wickets, with a best bowling of 4/7 against Kent.[4][5] She was again Surrey's leading wicket-taker in the 2019 Women's Twenty20 Cup, taking 9 wickets at an average of 13.55.[6] Gregory was also part of the Surrey side that won their first London Cup in 2020, putting in a "superb" spell of bowling to take 1/21.[7] She took four wickets for the side in the 2021 Women's Twenty20 Cup.[8] She took five wickets in the 2022 Women's Twenty20 Cup, at an average of 23.20.[9]
In 2020, Gregory played for South East Stars in the Rachael Heyhoe Flint Trophy. She appeared in 2 matches, taking 5 wickets at an average of 14.80. Her best bowling came in her second match, when she took 3/44 against Southern Vipers.[10][11] She was ever-present for the side in 2021, and helped the side to win the inaugural Charlotte Edwards Cup.[12] She took 6 wickets at an average of 35.66 in the Rachael Heyhoe Flint Trophy and 6 wickets at an average of 26.33 in the Charlotte Edwards Cup.[13][14] She also played six matches for Oval Invincibles in The Hundred, who went on to win the competition.[15][16] At the end of the 2021 season, it was announced that Gregory had signed a professional contract with South East Stars.[17] She played 13 matches for South East Stars in 2022, across the Charlotte Edwards Cup and the Rachael Heyhoe Flint Trophy, taking seven wickets.[18][19] She was also again part of the Oval Invincibles squad for The Hundred, but did not play a match.[20] Having joined the Southern Brave for 2023, she was on the winning side again in The Hundred and, again, did not play a match.[21] Meanwhile, for South East Stars in 2023, she was the third-leading wicket-taker in the Rachael Heyhoe Flint Trophy, with 21 wickets at an average of 17.80, as well as taking 7 wickets at an average of 15.14 in the Charlotte Edwards Cup.[22][23]
In June 2024, Gregory was selected by Manchester Originals in the Wildcard Draft for The Hundred 2024.[24] In 2024, she played 28 matches for South East Stars, across the Rachael Heyhoe Flint Trophy and the Charlotte Edwards Cup, taking 25 wickets.[25][26]