This is the listing of the 2020 Cash Calendar winners:
| Winning Day | First | Last | Calendar # | Amount |
| 3/31/2020 | Alex | Sears | 913 | $ 20.00 |
| 3/30/2020 | Robert | Cyr | 1374 | $ 20.00 |
| 3/29/2020 | Greg | Wry | 1943 | $ 20.00 |
| 3/28/2020 | Marti | McCaleb | 1569 | $ 50.00 |
| 3/27/2020 | Kimberly | Teer | 920 | $ 20.00 |
| 3/26/2020 | David | Gagnon | 906 | $ 20.00 |
| 3/25/2020 | Don | Keeler Jr | 1656 | $ 20.00 |
| 3/24/2020 | Dana | Bush | 1914 | $ 20.00 |
| 3/23/2020 | Georgia | Best | 400 | $ 20.00 |
| 3/22/2020 | Patty | Lawrence | 254 | $ 20.00 |
| 3/21/2020 | Patricia E | Brakeley | 1956 | $ 50.00 |
| 3/20/2020 | Sue | Record | 637 | $ 20.00 |
| 3/19/2020 | Louise | Warner | 280 | $ 20.00 |
| 3/18/2020 | Kathy | Mandigo | 1815 | $ 20.00 |
| 3/17/2020 | Ernest G | Gamache | 1548 | $ 150.00 |
| 3/16/2020 | Samantha | Foote | 1849 | $ 20.00 |
| 3/15/2020 | Bob | James | 1381 | $ 20.00 |
| 3/14/2020 | Tricia | Foster-Baccei | 665 | $ 50.00 |
| 3/13/2020 | Shirley T | Perkins | 353 | $ 20.00 |
| 3/12/2020 | Karen | Marshall | 936 | $ 20.00 |
| 3/11/2020 | Amara | Forgues | 1976 | $ 20.00 |
| 3/10/2020 | Monique | Bedard | 119 | $ 20.00 |
| 3/9/2020 | David | Holbrook | 551 | $ 20.00 |
| 3/8/2020 | Kathy | Laframboise | 878 | $ 20.00 |
| 3/7/2020 | Monica | Garthaffner | 1845 | $ 50.00 |
| 3/6/2020 | Amara | Forgues | 1976 | $ 20.00 |
| 3/5/2020 | Gail M | Smith | 1162 | $ 20.00 |
| 3/4/2020 | Debi | Barone | 1789 | $ 20.00 |
| 3/3/2020 | Frank & Lou | Miller | 1968 | $ 100.00 |
| 3/2/2020 | Taylor | Wisnowski | 597 | $ 20.00 |
| 3/1/2020 | Pat | Broughton | 658 | $ 20.00 |
| 2/29/2020 | Cindy | Kayhart | 461 | $ 50.00 |
| 2/28/2020 | Susan | Mclellan | 266 | $ 20.00 |
| 2/27/2020 | Lisa & Steve | Burlock | 113 | $ 20.00 |
| 2/26/2020 | Teri | Herzog | 626 | $ 20.00 |
| 2/25/2020 | Darin | Gallison | 1428 | $ 20.00 |
| 2/24/2020 | Ellen & John | Thompson Porter | 1811 | $ 20.00 |
| 2/23/2020 | Terence | Morris | 320 | $ 20.00 |
| 2/22/2020 | Donna | Laberge | 1555 | $ 50.00 |
| 2/21/2020 | Jeanette | Willey | 1657 | $ 20.00 |
| 2/20/2020 | Amy | Terrien | 1665 | $ 20.00 |
| 2/19/2020 | Kate | Barry | 1541 | $ 20.00 |
| 2/18/2020 | Donna | Quesnel | 166 | $ 20.00 |
| 2/17/2020 | Amey | Ryan | 1831 | $ 20.00 |
| 2/16/2020 | Liane | Barrera | 1530 | $ 20.00 |
| 2/15/2020 | Brian | Thomas | 1763 | $ 50.00 |
| 2/14/2020 | Diane | Many | 84 | $ 200.00 |
| 2/13/2020 | Ralph | Brown | 368 | $ 20.00 |
| 2/12/2020 | Ben | Lawton | 1112 | $ 20.00 |
| 2/11/2020 | Maureen | Conrad | 1651 | $ 20.00 |
| 2/10/2020 | Roberta | Leggett | 1049 | $ 20.00 |
| 2/9/2020 | Steve & Heidi | Whipple | 869 | $ 20.00 |
| 2/8/2020 | George | Tighe | 991 | $ 50.00 |
| 2/7/2020 | Lea | Stannard | 677 | $ 20.00 |
| 2/6/2020 | Brian | Saltzman | 567 | $ 20.00 |
| 2/5/2020 | B. | Roleau | 1874 | $ 20.00 |
| 2/4/2020 | Mark | McDonough | 415 | $ 20.00 |
| 2/3/2020 | Jordon | Broughton | 93 | $ 20.00 |
| 2/2/2020 | Genevieve | Miller | 1142 | $ 20.00 |
| 2/1/2020 | Betty & David | Lawson | 114 | $ 50.00 |
| 1/31/2020 | Ron & Mary Ann | Highter | 1800 | $ 20.00 |
| 1/30/2020 | Patty | Kelley | 1840 | $ 20.00 |
| 1/29/2020 | Dorothy | Gelinas | 1708 | $ 20.00 |
| 1/28/2020 | Heidi | Cunningham | 582 | $ 20.00 |
| 1/27/2020 | Patricia E | Brakeley | 1950 | $ 20.00 |
| 1/26/2020 | Debe | Fitzpatrick | 487 | $ 20.00 |
| 1/25/2020 | Nicholas | Rampulla | 651 | $ 50.00 |
| 1/24/2020 | Ann | Webster | 483 | $ 20.00 |
| 1/23/2020 | Dawn | Shepard | 1985 | $ 20.00 |
| 1/22/2020 | Tim & Jenni | Comiskey | 1584 | $ 20.00 |
| 1/21/2020 | Muriel | Harms | 516 | $ 20.00 |
| 1/20/2020 | Virginia | Bukowski | 768 | $ 20.00 |
| 1/19/2020 | Betsy | Magee | 68 | $ 20.00 |
| 1/18/2020 | Stella | Rader | 1494 | $ 50.00 |
| 1/17/2020 | Chantal | Gipson | 676 | $ 20.00 |
| 1/16/2020 | Saul & Alison | Nurok | 511 | $ 20.00 |
| 1/15/2020 | Theresa | Sullivan | 135 | $ 20.00 |
| 1/14/2020 | Caleb | Burkle | 537 | $ 20.00 |
| 1/13/2020 | Whitney Burgess | c/o Addison Co Real Estate | 864 | $ 20.00 |
| 1/12/2020 | Nicholas | Southworth | 110 | $ 20.00 |
| 1/11/2020 | Stephen | Ploof | 539 | $ 50.00 |
| 1/10/2020 | Walter | Ducharme | 426 | $ 20.00 |
| 1/9/2020 | Robert & Christine | Wagner | 1865 | $ 20.00 |
| 1/8/2020 | Brian | Saltzman | 569 | $ 20.00 |
| 1/7/2020 | Marilyn | Larocque | 752 | $ 20.00 |
| 1/6/2020 | Charlotte | Barnes | 1928 | $ 20.00 |
| 1/5/2020 | Townshend | Wenzler | 1786 | $ 20.00 |
| 1/4/2020 | Pete | Whittemore | 1824 | $ 50.00 |
| 1/3/2020 | Kelli Jo | Cloutier | 103 | $ 20.00 |
| 1/2/2020 | Wayne | Jaycox | 1443 | $ 20.00 |
| 1/1/2020 | Patrick | Michael | 1170 | $ 200.00 |
