| Date | Winner | Ticket Seller | Winning Prize |
| 05/01 | Diana Bowley | – | 4 WooSox tickets and Chipotle Dinner for 2 |
| 05/02 | Deb Ferranto | Sarah Meuse | $100 Wegman’s and $25 Dean Park Grill & Pizza |
| 05/03 | Sareena Kansra | Sameeha Anwar | $50 DCU Visa gift card and Mooyah Year of Free Meals |
| 05/04 | Lisa Rosenkrantz | Anna Rosenkrantz | $100 Cash |
| 05/05 | Matt Moriarty | Lilli Moriarty | Hanover Broadway Show pack for 4, Chipotle dinner for 2 |
| 05/06 | Sheila Birney | Mythania Anacassus | $200 Gift Card to Willy’s Steakhouse/Amici Trattora and $30 Gift Card to Dinky’s Blue Belle Diner |
| 05/07 | Robert Harnois | Charlotte Harnois | $100 Cash |
| 05/08 | Yogesh Bhardwaj | Aarushi Bhardwaj | Regatta Point Community Sailing Membership and Kayak Rental, and $20 Napoli Italian Deli |
| 05/09 | Bruno Cirilo | Emily Barros | $50 Sawa, $30 Dinky’s Blue Belle Diner, $20 Napoli Italian Deli |
| 05/10 | Anne Kiraithe | Maya Kiraithe | 1 Hour Massage at Elements Massage and Signature Manicure at Nicholas Michaels Spa |
| 05/11 | Ethan Suttinger | Ethan Suttinger | $100 Cash |
| 05/12 | Bob Quinn | Caroline Foley | $100 Home Depot gift card and 10″ decorated cake from Nothing Bundt Cakes |
| 05/13 | Julie Richard | Meghan Kalashian | $50 Burton’s Grill, $25 Lakeside Bar & Grill, $25 Gerardo’s Bakery |
| 05/14 | David White | Coach Kara White | $100 Cash |
| 05/15 | Maryum Zaidi | Sameeha Anwar | Family Membership to MA Audubon Society and $50 Hebert Candies gift card |
| 05/16 | Jeff Zidonis | Maxwell Brown | Core Connection – 3 class pass; Gift cards – Danielson’s Flowers $30, Texas Roadhouse $25 |
| 05/17 | Pankaj Sharma | Arushi Bhardwaj | $100 Wegman’s gift card, $25 Fandango gift card |
| 05/18 | Paul McDonald | Macy Kent | $100 cash |
| 05/19 | Julie Nason | Mark Ingersoll | $100 Coach gift card, $25 Ed Hyder’s Mediterranean Market gift card |
| 05/20 | Josh Rosen | Ellie Savoie | $50 Sawa gift card, $50 Tavern in the Square gift card |
| 05/21 | Sharyn Thomas | Ashley Thibeault | $100 cash |
| 05/22 | Xi Huan Zou | Anyee Li | Shrewsbury Club 3 month family membership, $50 Bloomin’ Brands gift card |
| 05/23 | Regina Hanson | Kamran Zaheer | $100 Olive Garden gift card, $25 Phantom Gourmet gift card |
| 05/24 | Kelly Lawlor | Charlotte Harnois | Dumpster Divers – 10 yard dumpster rental, $50 Wegman’s gift card |
| 05/25 | Lorraine Brezniak | Jarid Whitten | $100 cash |
| 05/26 | Deborah Quinn | Kelly Quinn | 2 Bliss Passes to Release Well-Being Center, Supercuts Hair Products Gift Basket |
| 05/27 | Nicole Smith | Matt Pellizari | Gift cards – $30 Vintage Grille, $25 Dean Park Grill & Pizza, 99 Restaurant $50 |
| 05/28 | Jo Willingham | Luke Willingham | $100 cash |
| 05/29 | Doris Sacalxot | Emily Barros | $50 Bloomin’ Brands gift card, 1 week WPI Rowing Camp |
| 05/30 | Stephanie Merchant | Mythania Anacassus | $50 DCU Visa gift card, Mooyah Year of Free Meals |
| 05/31 | Aarushi Bhardwaj | Audrey Liu | Marathon Sports $25 gift card plus gifts; 3 Class Pass to Core Connection |