This is the listing of 2026 Cash Calendar winners by day:
| Winning Day | First | Last | Calendar # | Amount |
| 1/1/2026 | Randy | Fleming | 1508 | $ 200.00 |
| 1/2/2026 | Steve | Aruzza | 131 | $ 20.00 |
| 1/3/2026 | Pat | Vaillancourt | 697 | $ 20.00 |
| 1/4/2026 | Hadley Financial Group | 1893 | $ 50.00 | |
| 1/5/2026 | Eric | Mortensen | 1814 | $ 20.00 |
| 1/6/2026 | Machelle | St. Pierre | 1183 | $ 20.00 |
| 1/7/2026 | Kyle | Koskinen | 847 | $ 20.00 |
| 1/8/2026 | Matt | Cutts | 1697 | $ 20.00 |
| 1/9/2026 | Martha | Bowdish | 542 | $ 20.00 |
| 1/10/2026 | Leslie | Armstrong | 1073 | $ 20.00 |
| 1/11/2026 | Heather | Plude | 1014 | $ 50.00 |
| 1/12/2026 | John | Fallon | 789 | $ 20.00 |
| 1/13/2026 | Kelli-Jo | Cloutier | 904 | $ 20.00 |
| 1/14/2026 | David | Cobb | 1212 | $ 20.00 |
| 1/15/2026 | Matt | Candon | 1021 | $ 20.00 |
| 1/16/2026 | Betty | Davis | 1957 | $ 20.00 |
| 1/17/2026 | Jill Fraga | Real Estate Co. of VT | 1329 | $ 20.00 |
| 1/18/2026 | Chelsea | Bashaw | 579 | $ 50.00 |
| 1/19/2026 | Lawrence | Volkert | 601 | $ 20.00 |
| 1/20/2026 | Max | Hirdler | 893 | $ 20.00 |
| 1/21/2026 | Jonas | Larocque | 202 | $ 20.00 |
| 1/22/2026 | Thomas | Blair | 472 | $ 20.00 |
| 1/23/2026 | Glen | Williams | 80 | $ 20.00 |
| 1/24/2026 | Carol Jane | Broughton | 651 | $ 20.00 |
| 1/25/2026 | Courtney | Laberge | 864 | $ 50.00 |
| 1/26/2026 | Donald | Keeler | 334 | $ 20.00 |
| 1/27/2026 | Henry | Stowe | 114 | $ 20.00 |
| 1/28/2026 | Jenne | Morton | 1510 | $ 20.00 |
| 1/29/2026 | Karen | Lyons | 873 | $ 20.00 |
| 1/30/2026 | Matt | Kardas | 1230 | $ 20.00 |
| 1/31/2026 | Lanpher Construction | 1981 | $ 20.00 | |
| 2/1/2026 | Cindy | Atkins | 528 | $ 50.00 |
| 2/2/2026 | Connie | Connors | 871 | $ 20.00 |
| 2/3/2026 | Claire | Groby | 1417 | $ 20.00 |
| 2/4/2026 | Mark | Jacobson | 1351 | $ 20.00 |
| 2/5/2026 | Paul | Bougor | 473 | $ 20.00 |
| 2/6/2026 | Chad & Krista | Scarborough | 1911 | $ 20.00 |
| 2/7/2026 | Tim | Allen | 101 | $ 20.00 |
| 2/8/2026 | Logan | Seaburg | 852 | $ 50.00 |
| 2/9/2026 | Peg | Cobb | 1738 | $ 20.00 |
| 2/10/2026 | Steve | Butterfield | 1706 | $ 20.00 |
| 2/11/2026 | Leia | Broughton | 656 | $ 20.00 |
| 2/12/2026 | Jenny & Devlin | Harding | 1134 | $ 20.00 |
| 2/13/2026 | Ron & Evelyn | Martell | 1687 | $ 20.00 |
| 2/14/2026 | Lynn | Wolfe | 1452 | $ 200.00 |
| 2/15/2026 | David | Kerr | 10 | $ 50.00 |
| 2/16/2026 | Carolyn | VanVleck | 1789 | $ 20.00 |
| 2/17/2026 | Jonathan | Dinub | 623 | $ 20.00 |
| 2/18/2026 | Debbie | Goodrich | 625 | $ 20.00 |
| 2/19/2026 | Liam | Curtis | 702 | $ 20.00 |
| 2/20/2026 | Jim | Hadeka | 1901 | $ 20.00 |
| 2/21/2026 | Bill | Kernan | 1285 | $ 20.00 |
| 2/22/2026 | Sherry | Bristol | 1423 | $ 50.00 |
| 2/23/2026 | Tom | Howard | 838 | $ 20.00 |
| 2/24/2026 | Charlie | Smith | 1689 | $ 20.00 |
| 2/25/2026 | Ronald G. | Payne | 1185 | $ 20.00 |
| 2/26/2026 | Gary | Starr | 1178 | $ 20.00 |
| 2/27/2026 | James | Lawrence | 292 | $ 20.00 |
| 2/28/2026 | Holly | Noordsy | 1551 | $ 20.00 |
