(Formerly Ladies Singles – Repurposed in 2014 for LADIES DOUBLES)
Given in memory of former MIYC members and avid tennis devotee, Jean Hamilton
| 1982 | Nancy Conley | 1997 | Susan Moffett |
| 1983-84 | Carol Connor | 1998 | Kim McGee |
| 1985 | Judy Reige | 1989-90 | Carol Connor |
| 1986 | Linda Watkins | 2014 | Nancy Collins, Megan Stuart |
| 1987 | Dagny St. John | 2015 | Nancy Collins, Megan Stuart |
| 1988 | Linda Watkins | 2016 | Heather Castle, Anna Foster |
| 1989-90 | Carol Connor | 2017 | Megan Stuart, Suzie Turley |
| 1991-92 | Amy Hallberg | 2018 | Rebecca Halsey, Nancy Collins |
| 1993-94 | Susan Moffett | 2019 | Ellie Hughes, Avery Hughes |
| 1996 | Dagny St. John |