SADDEST
| Date | Clue |
|---|---|
| 2021-10-31 | Farthest down? |
| 2008-12-04 | Most blue |
| 2007-10-08 | Most mournful |
| 2004-07-28 | Most blue |
| 2002-09-23 | Most forlorn |
| 2000-03-18 | Lower than the rest |
| 1998-06-04 | Most pathetic |
| 1995-08-30 | Most deplorable |
| 1994-12-15 | Most downcast |
| 1994-08-14 | Most dolorous |