2022
| Tournament Name | Winner | Runner-up |
| Jr. Tennis Tournament
(High School & College) |
Nicole Waldron and Drew Redman
|
Scottie Doherty & Charlotte Garrity
|
| Men’s Singles
|
Jay Sharman
|
Todd Johnston
|
| Bergstrom Cup
(Mixed Doubles) |
John Casassa & Michelle Waldron
|
Amy Naples & Art Queenan |
| Father-Daughter |
|
|
| Married Couples | Denise & John Wright
|
Kathy & Jeff Berardi |
| Mother-Daughter
|
|
|
| Helen Queenan Woman’s Doubles
|
Amy Naples & Sally Holway |
Lisa McCarthy & Mary Rife
|
| Mother-Son
|
Casey & Kelly Fennel
|
Gavin and Kathy Berardi |
| Tiny Gregg A Team
|
Gavin Berardi & Jack Foley |
Grace Doyle & Casey Fennell |
| Tiny Gregg B Team
|
Riley Fennell & Ben Buckley |
Claire Buckley & James Zilinski
|
| Men’s Doubles Holway Cup
|
Dave Goulet & Jeff Berardi
|
John C & John Wright
|
| Father-Son |
|
2021
| Tournament Name | Winner | Runner-up |
| Jr. Tennis Tournament
(High School & College) |
Nicole Waldron and John E. Adams
|
Michelle Waldron and Jack Perry
|
| Men’s Singles
|
Jay Sharman
|
Todd Johnston
|
| Bergstrom Cup
(Mixed Doubles) |
Kelly Fennel & Jeff Berardi
|
Lauren Doherty & Richard Holway |
| Father-Daughter | Charlotte & Billy Garrity
|
Abby & Art Queenan
|
| Married Couples | Denise & John Wright
|
Kathy & Jeff Berardi |
| Mother-Daughter
|
Charlotte & Sarah Garrity
|
Lily & Krista Riley |
| Helen Queenan Woman’s Doubles
|
Amy Naples & Deanna Waldron
|
Susan Armo & Lauren Doherty
|
| Mother-Son | ||
| Tiny Gregg A Team
|
Lily Riley & Gavin Berardi
|
Charlotte Garrity & Drew Redman & |
| Tiny Gregg B Team
|
Emma Zilinski & Ben Buckley
|
Nora Rodes & Jack Foley
|
| Men’s Doubles Holway Cup
|
Jay Sharman & Billy Garrity
|
Todd Johnston & Peter Waldron
|
| Father-Son | Gavin & Jeff Berardi
|
Aiden & Jeff Doyle |
2020
| Tournament Name | Winner | Runner-up |
| Mother-Daughter
|
Sarah & Charlotte Garrity
|
Grace & Rose Doyle |
| Father-Daughter
|
Grace & Jeff Doyle
|
Caitlin & Jeff Berrardi |
| Father-Son
|
Connor & Art Queenan
|
Jeff & Gavin Berardi |
| Mother-Son | Ben & Sarah Garrity
|
Scottie & Lauren Doherty |
| Helen Queenan Woman’s Doubles
|
Amy Naples and Lisa McCarthy | Ruzanna Queenan and Ellen Papcy |
| Tiny Gregg A Team
|
Ben Garrity and Drew Redman | Casey Fennell and Janel Sharman |
| Tiny Gregg B Team
|
Gavin Berardi and Jack Foley | Ben Buckley and Brady Chase |
| Bergstrom Cup
|
Jane Redman & Jeff Berardi
|
Ruz Queenan & Todd Johnston |
| Jr. Tennis Tournament
(High School & College) |
Michelle Waldron & Ben Garrity
|
Ally Egan & John Adams |
| Men’s Singles
|
Jay Sharman | Todd Johnston |
| Men’s Doubles Holway Cup
|
Dave Goulet and Richard G. Holway | Jeff Berardi and Patrick Conran |
| Married Couples | Denise & John Wright
|
Ruz & Art Queenan |
2019 Season
| Tournament Name | Winner | Runner-up |
| Mother-Daughter
|
Kelly Fennell & Janel Sharman
|
Sarah & Charlotte Garrity |
| Father-Daughter
|
Jeff and Caitlin Berardi
|
Jeff & Grace Doyle |
| Father-Son
|
Art & Connor Queenan
|
Tom & Jake Leire |
| Mother-Son | Ruzanna & Connor Queenan
|
Sarah & Ben Garrity
|
| Helen Queenan Woman’s Doubles
|
Amy Naples & Nancy Aral | Deanna Waldron & Kelly Fennell |
| Tiny Gregg A Team
|
Charlotte Garrity & Max Niit
|
John Redman & Janel Sharman |
| Tiny Gregg B Team
|
Drew Redman & Tyler Zilinski
|
Grace Doyle & Nora Sharman |
| Bergstrom Cup
|
Rachel Palumbo & Todd Johnston
|
Amy Naples & John Casassa |
| Jr. Tennis Tournament
(High School & College) |
Nicole Waldron & Charlie Bardenheuer
|
Michelle Waldron &
Jack Perry
|
| Men’s Singles
|
Todd Johnston | Jay Sharman |
| Men’s Doubles Holway Cup
|
Jeff Berardi & Champe Fisher
|
Ricky Holway & John Correnti |
| Married Couples | Denise & John Wright | King & Lauren Doherty |
2018 – Last Season
| Tournament Name | Winner | Runner-up |
| Mother-Daughter
|
Sarah & Charlotte Garrity
|
Krista & Lily Riley |
| Father-Daughter
|
Pepper & Lilly Riley
|
Bill & Charlotte Garrity |
| Father-Son
|
||
| Ladies Doubles
|
||
| Tiny Gregg A Team
|
John Adams and Max Niit |
Connor Queenan and Harrison Smith |
| Tiny Gregg B Team
|
||
| Bergstrom Cup
|
Sally Holway & Art Queenan
|
Ruz Queenan & Ricky Holway |
| Men’s Singles
|
Todd Johnston
|
John Adams |
| Men’s Doubles Holway Cup
|
Jeff & Berardy Ricky Holway
|
Art Queenan & John Adams |
| Married Couples |
2017 Season
| Tournament Name | Winner | Runner-up |
| Mother-Daughter
|
Deanna Waldron & Catherine Callanan | Jennifer & Caroline Leire |
| Father-Daughter
|
Lars & Abby Niit | Lili & Pepper Riley |
| Father-Son
|
John & Johnny Adams | Lars & Eric Niit |
| Ladies Doubles
|
Sarah Garrity & Jane Redman | Nada Bric & Deanna Waldron |
| Tiny Gregg A Team
|
|
|
| Tiny Gregg B Team
|
Catherine Callanan & Bryan Herlihy | Caroline Leire & Grace Doyle |
| Bergstrom Cup
|
Denise Wright & Don Perry | Deanna Waldron & Jeff Berardi |
| Men’s Singles
|
Todd Johnston | John Adams |
| Men’s Doubles Holway Cup
|
Dave Goulet & King Doherty | Lars Niit & Alan Pond |
| Married Couples |
2016 Season
| Tournament Name | Winner | Runner-up |
Mother-Daughter |
Kate and Tori Egan | Deanna Waldron and Cate Callahan |
| Father-Daughter
|
Peter and Nicole Waldron | Lars and Abigale Niit |
| Father-Son
|
John & John Adams | Jake Leire & Paul Mastroianni |
| Ladies Doubles
|
Nancy Aral and Deanna Waldron | Sally Holway and Jane Redman |
Tiny Gregg A Team |
Ali Egan & Nicole Waldron | Eric Niit & Aiden Callanan |
Tiny Gregg B Team |
John Redman & Brian Herlihy | Harrison Carven & Kate Garrity |
| Bergstrom Cup
|
John Adams and Amy Simon | Arthur Queenan and Denise Wright |
| Men’s Singles | Todd Johnston | Art Queenan |
| Men’s Doubles Holway Cup | John Adams & Frank Kodzis | Todd Johnson & Colin Diver |
| Married Couples | Lauren & King Doherty | Noreen and Paul Mastroianni |
2015 – Past Season
| Tournament Name | Winner | Runner-up |
| Mother-Daughter | Deanna and Nicole Waldron | Amy Naples and Tori Egan |
| Father-Daughter | Peter and Nicole Waldron | Don Holway and Ali Egan |
| Father-Son | Ryan and Paul Mastroainni | Connor and Brendan Herlihy |
| Ladies Doubles | Nini Holway & Amy Naples | Nada Bric & Sarah Garrity |
| Tiny Gregg A Team | Tommy Leire & Aiden Callanan | John Adams & Olivia Smith |
| Tiny Gregg B Team | Conner Herlihy & Max Niit | John Adams & John Redman |
Bergstrom Cup |
Todd Johnson and Deanna Waldron | Alan Pond and Jeannine Holway |
| Men’s Singles | Todd Johnson | King Doherty |
| Men’s Doubles Holway Cup | GeorgeThibault and George Doherty | Don Holway and Lars Niit |
| Married Couples | Noreen and Paul Mastroianni | Suzanne and Patrick Conran |
2014 – Past Season
| Tournament Name | Winner | Runner-up |
| Mother-Daughter | Denise Wright and Michelle Waldron | Deanna Waldron and Nicole Waldron |
| Father-Daughter | Alan Pond and Michelle Waldron | Don Holway and Anna Garrity |
| Father-Son | King Doherty and Jake Doherty | Ricky Holway and Ryan Mastroianni |
| Ladies Doubles | Jane Redman and Nada Bric | Denise Wright and Deanna Waldron |
| Tiny Gregg A Team | Nicole Waldron and Harrison Smith | Charlie Bardenheauer and Erik Niit |
| Tiny Gregg B Team | Ben Garrity & Abi Niit | Scott Doherty and Aiden Callahan |
| Bergstrom Cup | Alan Pond and Lauren Doherty | Ricky Holway and Laura Bergeron |
| Men’s Singles | John Adams | King Doherty |
| Men’s Doubles Holway Cup | Brian Herlihy and Rick Holway | Don Perry and Alan Pond |
| Married Couples | King and Lauren Doherty | Jeff and Jane Redman |
2013 – Past Season
| Tournament Name | Winner | Runner-up |
| Mother-Daughter | Denise Wright and Nicole Waldron | Deanna Waldron and Michelle Waldron |
| Father-Daughter | Peter Waldron and Michelle Waldron | Don Holway and Nicole Waldron |
| Father-Son | King Doherty and Jake Doherty | Paul Mastroianni and Ryan Mastroianni |
| Ladies Doubles | Nada Bric and Denise Wright | Margarite Correnti and Sarah Garrity |
| Tiny Gregg A Team | Ryan Mastroianni and Charlie Bardenheur | Chris Mastroianni and Nicole Waldron |
| Tiny Gregg B Team | Erik Niit and Connor Herlihy | Erik Niit and Ben Garrity |
Bergstrom Cup |
Amy Sharman Naples and John Wright | Jane Redman and King Doherty |
| Men’s Singles | John Wright | King Doherty |
Men’s Doubles Holway Cup |
Al Pond and Ray Brown | King Doherty and Patrick Conran |
| Married Couples | Lauren and King Doherty | Jen & David Anderson |