| KENJENNINGS | 2004 Jeopardy! contestant who still holds the record for most money won in regular-season play ($2 520 700): 2 wds. |
| CHANG | Who still holds the record for being the youngest man in history to win any Grand Slam? (5) |
| GELT | Money won in a game of dreidel |
| JAMESHOLZHAUER | 2019 Jeopardy! contestant who nearly broke the record and is #2 in regular-season winnings ($2 462 216): 2 wds. |
| OCTS | Post-season play mos. |
| DAVIDMADDEN | 2005 Jeopardy! contestant who is now #3 in regular-season winnings ($432 400): 2 wds. |
| BEAMON | 1968 Olympic longjump champion who still holds the Olympic record, Bob ... (6) |
| DRAWS | Schedules for a season's play in football, basketball or baseball |
| THEWINTERSTALE | Article that's cliche-ridden about season's play |
| HERMANNPAUL | Herr Muller, who won races on two, three, and four wheels, and still holds the record for being the oldest ever motorcycle world champion. (7,4) |
| TYSON | "Mike ___". youngest heavyweight boxing champion from the US (still holds the record today) (5) |
| ADMIRAL | The head of the Le Strange family of Hunstanton still holds the hereditary title of Lord High .... of the Wash (7) |
| TOPOFTHESCALE | Tip pertaining to come from the barman? Drink the most money one can expect to get! (3,2,3,5) |
| TREKKER | "To boldly go" fan but who still has both feet on the ground in the real world! (7) |
| RICHEST | Right one with the box is the one with the most money (7) |
| MONDAY | Get most money on day considered the start of the working week (6) |
| RICHESTNUTS | Eccentric folks with the most money in Providence? |
| IAN | Original EastEnders character who still lives in the Square, --- Beale (3) |
| INNINGS | Money won from bet after wicket falls in spell at the crease (7) |
| PURSE | Gather up the money won (5) |
