Our history dates back to 1972 when the Toronto & District Women's Squash League was a part of the Ontario Ladies Squash Racquets Association (OLSRA). The photo above is from the cover of the October 1975 Newsletter of the OLSRA.
Below is a partial history of more than 40 years of TDWSA League Champions and leaders (arranged chronologically by decade). If you have information that can help us fill in the gaps in our records, or stories from seasons past that you would like to share, please contact us.
2010s
| Year | A | B | C | D | E | Executive |
| 2018/19 | GoodLife Dunfield | One Health Club | Ontario Racquet Club | Metro YMCA | Aswathy Mathew | Elka Markus, Christine Horner, Vanessa Thoo, Kathy Rintoul, Alison LeBer, Carol Reilly, Niki Aron, Cari Fraser, Carolyn Vranesic, Anna Tomei, Carolyn Feather, Donna Thompson, Wendy Train, Gabrielle Amoroso, Carol Johnston, Liz McBeth (exiting chair) |
| 2017/18 | Executive Squash & Fitness | Ontario Racquet Club | GoodLife Dunfield | Ontario Racquet Club | Simone Visram | Liz McBeth, Christine Horner, Vanessa Thoo, Alison LeBer, Bridgette Badalamenti, Carolyn Vranesic, Anna Tomei, Carolyn Feather, Donna Thompson, Julie Hisey, Elka Markus |
| 2016/17 | Ontario Racquet Club | One Health Club | RCYC 1 | Badminton & Racquet Club | Hannah Chan | Liz McBeth, Christine Horner, Alison LeBer, Bridgette Badalamenti, Sue Murphy, Anna Tomei, Carolyn Feather, Alexa May/Donna Thompson, Julie Hisey, Elka Markus |
| 2015/16 | Executive Squash & Fitness | GoodLife Valhalla | RCYC | n/a | n/a | Carolyn Moss, Sarah Jane Cresswell, Anna Tomei, Sue Murphy, Carolyn Feather, Liz McBeth, Alison LeBer |
| 2014/15 | Toronto Blues | Mayfair Lakeshore | Mayfair Lakeshore | Executive Squash & Fitness | n/a | Carolyn Moss, Sarah Jane Cresswell, Anna Tomei, Sue Murphy, Carolyn Feather, Sue Bettencourt |
| 2013/14 | Ontario Racquet Club | GoodLife Valhalla | Executive Squash & Fitness | Club Meadowvale | n/a | Carolyn Moss, Sarah Jane Cresswell, Anna Tomei, Sue Murphy, Carolyn Feather, Sue Bettencourt |
| 2012/13 | Executive Squash & Fitness | GoodLife Parkview | RCYC | Crescent Town | n/a | Brenda Forbes, Sarah Jane Cresswell, Anna Tomei, Sue Murphy, Carolyn Feather, Sue Bettencourt |
| 2011/12 | The Granite Club | Executive Squash & Fitness | Mayfair Lakeshore | RCYC | n/a | Brenda Forbes |
| 2010/11 | The Granite Club | Mayfair Lakeshore | National Squash Academy | Pickering Squash Club | n/a | Brenda Forbes, Rita Bloem, Carolyn Moss, Carolyn Feather, Kelly Williamson, Donna Thompson, Sue Murphy |
| 2009/10 | Badminton & Racquet Club | Mayfair Lakeshore | Glendon Athletic Club | Ontario Racquet Club | n/a | Brenda Forbes, Rita Bloem, Carolyn Moss, Carolyn Feather, Donna Thompson |
2000s
| Year | A | B | C | D | Executive |
| 2008/09 | Not known | Badminton & Racquet Club | Glendon Athletic Club | Fabulous Fitness | Brenda Forbes, Rita Bloem, Carolyn Moss, Shannon Fisher, Julie, Donna Thompson, Carolyn Feather |
| 2007/08 | Fabulous Fitness | ORC | RCYC | RCYC | Jennifer Bennett, Rita Bloem, Shannon Fisher, Julie, Donna Thompson, Carolyn Feather, Carolyn Moss (prizes) |
| 2006/07 | Fabulous Fitness | GoodLife Parkview | The Dunfield Club | Fabulous Fitness | Jennifer Bennett, Rita Bloem, Shannon Fisher, Julie, Donna Thompson, Carolyn Feather, Carolyn Moss (prizes) |
| 2005/06 | Fabulous Fitness | U of T | Pickering Squash Club 1 | Glenway | Jennifer Bennett, Donna Thompson |
| 2005 | Pickering Squash Club | ORC | U of T | Burlington F&R | Jennifer Bennett, Donna Thompson |
| 2004 | Pickering Squash Club | Northridge Club | Glendon Athletic Club | Shapes - Scarborough | Jennifer Bennett, Donna Thompson |
| 2003 | Mayfair Lakeshore | Fitness Institute Mississauga | Pine Valley Racquets Club | Richmond Hill | Doreen Hunt, Donna Thompson |
| 2002 | Mayfair Lakeshore | Not known | Fitness Institute West | Richmond Hill | Donna Thompson |
| 2001 | Mayfair Lakeshore | RCYC | Club Markham | Not known | Donna Thompson |
| 2000 | Mayfair Lakeshore | Cedar Springs | U of T | Balmy Beach | Donna Thompson |
1990s
| Year | A | B | C | D | Executive |
| 1999 | Mayfair Lakeshore | Pickering Squash Club | Not known | Pickering Squash Club | Donna Thompson |
| 1998 | Mayfair Lakeshore | Cedar Springs | Granite Club | Pickering Squash Club | Elka Markus, Susan, Doreen, Joan |
| 1997 | Mayfair Lakeshore | Adonis Club | Regency Racquets Club | Cedar Springs | Teresa Miolla |
| 1996 | Pine Valley Racquet Club | Not known | Cedar Springs | n/a | Teresa Miolla |
| 1995 | Pine Valley Racquet Club | Not known | The Skyline Club | n/a | Teresa Miolla |
| 1994 | Not known | Not known | Not known | n/a | Not known |
| 1993 | Mayfair Lakeshore | Ajax Squash Club | The Granite Club | n/a | Not known |
| 1992 | Mayfair Lakeshore | Toronto Cricket Club | Northridge Club | Regency Racquets Club | Not known |
| 1991 | Not known | Glendon Squash Club | The Skyline Club | n/a | Not known |
| 1990 | Toronto Athletic Club | Mayfair Lakeshore | Ontario Racquet Club | n/a | Not known |
1980s
| Year | A | B | C | D | Executive |
| 1989 | Mayfair Lakeshore | n/a | Toronto Athletic Club II | Richmond Hill | Not known |
| 1988 | Ajax Squash Club | n/a | Georgetown | n/a | Not known |
| 1987 | U of T | n/a | n/a | n/a | Not known |
| 1986 | The Club | n/a | n/a | n/a | Not known |
| 1985 | Mayfair Parkway 1 | n/a | n/a | n/a | Not known |
| 1984 | Mayfair North | n/a | n/a | n/a | Not known |
| 1983 | Mayfair North | n/a | n/a | n/a | Not known |
| 1982 | Mayfair Parkway 1 | n/a | n/a | n/a | Not known |
| 1981 | Bridlewood 1 | n/a | n/a | n/a | Ann Thompson, Ramola Vishnu, Heather Probert, Marie Priest, Mary Mitchell, Paula Vine, Sharon McKenna, Rita King, Sura Hall, Maggie Caton |
1970s
| Year | A | B | C | D | Executive |
| 1979/80 | Bridlewood 1 | n/a | n/a | n/a | Ann Thompson, Laurie Grant, Heather Probert, Jean Patterson, Paula Vine, Rita King, Sura Hall |
| 1978/79 | Mayfair Club | n/a | n/a | n/a | Susan Jewitt, Ann Thompson, Janet Atkinson |
| 1977/78 | Mayfair North | n/a | n/a | n/a | Not known |
| 1976/77 | Toronto Squash 1 | n/a | n/a | n/a | Bev Bowen, Lottie Allison, Penny Ball, Marta Raymore, Jessie Smalley |
| 1975/76 | Toronto Lawn 1 | n/a | n/a | n/a | Ann Thompson, Bev Bowen, Joan Hulmston, Linda Gray, Gwen Dugan, Ann Thompson, Bobbe Frost, Laney Marshall |
| 1974/75 | Toronto Cricket Club | n/a | n/a | n/a | Ann Thompson |
| 1973/74 | Not known | n/a | n/a | n/a | Not known |
| 1972/73 | Not known | n/a | n/a | n/a | Not known |