Jessie Fleming is a professional footballer from CAN and is currently 29 years old. He is on the books of Portland Thorns FC Women and wears shirt number 21. At international level, he features for Canada Women. His main role on the pitch is Midfield. He measures 161cm in height and weighs 56kg.

His latest transfer saw him join Chelsea FC Women from UCLA Women via Free on 2020-07-01.

Over 27 appearances in the United States Women's National Soccer League 2025, Jessie Fleming contributed 2 goals and 5 assists, completed 27 key passes from 673 total passes, and posted a passing accuracy of 18.9.