Miss Gay Massachusetts USofA is a prelim to Miss Gay USofA.
Miss Gay Massachusetts USofA Titleholders
Joanna James 
Billie Jean 
Lakia Mondale 
Margeaux Powell Haze 
Kira Stone 
Ania Bangkoks – Photo by Ivy League-O’deria 
Khloe Glamoure – Photo by Jess Razzi 
Bang – Photo by Branden Marcus 
Qya Cristál – Photo by Clarence Mowglii Morton 
Ivy League
Miss Gay Massachusetts USofA Titleholders
- 1992 – Joanna James
- 1994 – Billie Jean
- 1996 – Lakia Mondale
- 2013 – Margeaux Powell Haze
- 2014 – Kira Stone
- 2015 – Ania Bangkoks
- 2016 – Khloe Glamoure
- 2017 – Bang
- 2018 – Qya Cristál
- 2019 – Ivy League
Miss Gay Massachusetts USofA History
- 1992
- Winner – Joanna James
- 1993
- Needs researched.
- 1994
- Winner – Billie Jean
- 1995
- Needs researched.
- 1996
- Winner – Lakia Mondale
- 1997 – 2012
- Needs researched.
- 2013
- Winner – Margeaux Powell Haze
- 2014
- Winner – Kira Stone
- 2015
- Winner – Ania Bangkoks
- 2016
- Winner – Khloe Glamoure
- 2017
- Winner – Bang
- 1st Alternate – Kamden T. Rage
- 2018
- 2019
- Winner – Ivy League
- 1st Alternate – Buffy Halliwell
- Archive: Miss Gay Massachusetts USofA | The Crown & Anchor (Provincetown, Massachusetts) | 4/14/2019
- 2020
- Archive: Miss Gay Massachusetts USofA | The Crown & Anchor (Provincetown, Massachusetts) | 4/18/2020
- Notes: Event was cancelled due to Covid-19 (Coronavirus) pandemic.