| Date | Weekday | Amount | Winner | Sold by | Drawn by |
| June 1, 2009 | Monday | $50 | Janet Murphy | Justin Silvestro | Steve Hanley |
| June 2, 2009 | Tuesday | $50 | Andrea LaFrance | Josh Weissman LaF. | Jody Grifone |
| June 3, 2009 | Wednesday | $50 | Tom Ferrari | Dereck Ferrari | Wendy Fournier |
| June 4, 2009 | Thursday | $50 | Andrea LaFrance | Josh Weissman LaF. | Ann Poulos |
| June 5, 2009 | Friday | $50 | Frank Callahan | Charley O'Callaghan | Leslie Ackan |
| June 6, 2009 | Saturday | $100 | Liz Check | Luke Check-Davis | Edmund Becker |
| June 7, 2009 | Sunday | $100 | Mary Stanowicz | Garrett Stanowicz | Cathy McCassie |
| June 8, 2009 | Monday | $50 | Bobby Kelly | Adam Wetherbee | Julianna Cacciatore |
| June 9, 2009 | Tuesday | $50 | Dan McKenzie | Adam Wetherbee | Doreen Gulledge |
| June 10, 2009 | Wednesday | $50 | Jon Schroeder | Alex Morrissey | Dawn Rice |
| June 11, 2009 | Thursday | $50 | Juliette Noonan | T.J. Noonan | L. Wunevman |
| June 12, 2009 | Friday | $50 | Ann Poulos | Joey Fournier | Joan Ferrari |
| June 13, 2009 | Saturday | $100 | Tony Campagna | Anthony Campagna | Brian Millerick |
| June 14, 2009 | Sunday | $100 | Toni Groholski | Jeffrey MacEwen | L. Humbert |
| June 15, 2009 | Monday | $50 | John McDonald | T.J. Noonan | Gloria Babigian |
| June 16, 2009 | Tuesday | $50 | Paul Stanowicz | Garrett Stanowicz | Laban Christenson |
| June 17, 2009 | Wednesday | $50 | Sean Reynolds Family | Sean Reynolds | Jackie Leclaire |
| June 18, 2009 | Thursday | $50 | Dave Vitone | Tyler Zanco | Diane Brhils |
| June 19, 2009 | Friday | $50 | Denise Lopriore | Larry Salvucci | Dareen Zoelly |
| June 20, 2009 | Saturday | $100 | Paul Gagne | Ryan LaFauce | Samantha Dronhn |
| June 21, 2009 | Sunday | $100 | George Millerick | Shane Millerick | Lilu Vasquez |
| June 22, 2009 | Monday | $50 | Mario Cavallaro | ??????? | Jacob Poirier |
| June 23, 2009 | Tuesday | $50 | Patricia Muccioli | Tyler Trelegan | Theresa E. Minni |
| June 24, 2009 | Wednesday | $50 | Katelyn Abruzzi | Ben MacEwen | Danny Lawsen |
| June 25, 2009 | Thursday | $50 | Virginia Hays | T.J. Noonan | Dan MacDougal |
| June 26, 2009 | Friday | $50 | Theresa Bella | Nick Bella | Donald J.Noull |
| June 27, 2009 | Saturday | $100 | Lauren Murphy | Justin Silvestro | Tiana Babigian |
| June 28, 2009 | Sunday | $100 | Marc Rizza | Rion Hallaran | Theresa Bella |
| June 29, 2009 | Monday | $50 | Cathy McCassie | Ryan McCassie | Jessica Pelletier |
| June 30, 2009 | Tuesday | $1,000 | Kristen Libertini | Michael Libertini | Amanda Medino |