| 100% | POUNDFOOLISH | 12 | Not good with large sums of money, in a saying |
| 46% | DONATION | 8 | Sum of money given to a good cause |
| 45% | DONATION | 8 | Sum of money given to a good or worthy cause |
| 41% | WAD | 3 | Large sum of money |
| 41% | PRETTYPENNY | 11 | Large sum of money |
| 41% | BAG | 3 | Large sum of money, nowadays |
| 40% | OKBYME | 6 | "I'm good with it," or a description of eight occurrences in this puzzle |
| 39% | PARALEGAL | 9 | Works with law but not in the level of a lawyer |
| 39% | THEDEVILYOUKNOW | 15 | Better adversary to deal with, in a saying |
| 39% | BALANCE | 7 | Amount of money in a bank account |
| 38% | RAKEIN | 6 | Earn tons of, as a large sum of money (2 wds.) |
| 38% | STAKE | 5 | Sum of money risked by a gambler |
| 38% | LOAN | 4 | Sum of money borrowed from a bank |
| 38% | COG | 3 | ___ in the machine, phrase associated with machines that means "small part of a large organization" |
| 38% | LETMEGUESS | 10 | Words from someone with a good idea of what you’re about to say |
| 37% | WINSTAR | 7 | ___ World Casino is the largest casino in America with a total of 1495 rooms |
| 37% | MADEBANK | 8 | Earned lots of money in a short time: 2 wds. |
| 37% | ROADS | 5 | In a saying, all of them lead to Rome |
| 37% | TUITION | 7 | Sum of money charged for a term at university |
| 37% | SAVE | 4 | Put money in a piggy bank, say |
| 37% | DYLAN | 5 | About whom Obama said "There is not a bigger giant in the history of American music" |
| 36% | SOFA | 4 | Large piece of furniture in a man cave |
| 36% | NESS | 4 | Loch ___ Monster, large mysterious cryptid said to inhabit the depths of a lake in the Scottish Highlands |
| 36% | ASHE | 4 | ___ Stadium, venue with a cushioned acrylic surface that is the largest of its type in the world |
| 36% | DIVIDEND | 8 | A sum of money paid periodically |
| 36% | CURRENCY | 8 | System of money in use in a specific country |
| 36% | TIME | 4 | It's money, in a saying |
| 35% | PEANUTS | 7 | Informal way of saying a very small sum of money |
| 35% | BARTER | 6 | Make a trade with goods or services instead of money |
| 35% | CASHFLOW | 8 | The movement of money in and out of a company |