| Text | Length |
| Gambling establishment | 22 |
| Gambling dice game | 18 |
| Gambling device | 15 |
| Gambling destination | 20 |
| Gambling debts | 14 |
| Gambling debt, so to speak | 26 |
| Gambling debt, slangily | 23 |
| Gambling cubes | 14 |
| Gambling cube | 13 |
| Gambling column's long shot winner | 38 |
| Gambling city near Lake Tahoe | 29 |
| Gambling city | 13 |
| Gambling chain that closed its doors in 2010 | 44 |
| Gambling center | 15 |
| Gambling casino word | 20 |
| Gambling bug, e.g. | 18 |
| Gambling bet that picks the top two finishers in a race | 55 |
| Gambling baseballer? | 20 |
| Gambling asset | 14 |
| Gambling area | 13 |
| Gambling and drinking, e.g. | 27 |
| Gambling and cards expert John | 30 |
| Gambling and boozing, for two | 29 |
| Gambling and boozing | 20 |
| Gambling aids | 13 |
| Gambling actor? | 15 |
| Gambling destination | 21 |
| Gambling | 8 |
| Gamblin' man | 16 |
| Gambles that don't involve the house | 40 |
| Gambles on a market drop | 24 |
| Gambles in a way | 16 |
| Gambles heavily | 15 |
| Gambles | 7 |
| Gamblers' venue (Abbr.) | 27 |
| Gamblers' setbacks | 22 |
| Gamblers' paradise | 22 |
| Gamblers' option, briefly | 29 |
| Gamblers' option briefly | 29 |
| Gamblers' NYC hangout | 25 |
| Gamblers' notes | 19 |
| Gamblers' methods | 21 |
| Gamblers' mecca | 19 |
| Gamblers' markers | 21 |
| Gamblers' letters | 21 |
| Gamblers' informers | 23 |
| Gamblers' holdings | 22 |
| Gamblers' haunts, briefly | 29 |
| Gamblers' giveaways | 23 |
| Gamblers' game | 18 |
| Gamblers' card game | 23 |
| Gamblers rack them up | 21 |
| Gamblers place them | 19 |
| Gambler, Ohio, campus | 21 |
| Gambler, in old Rome | 20 |
| Gambler's words of lament | 29 |
| Gambler's words | 19 |
| Gambler's woe | 17 |
| Gambler's wager | 19 |
| Gambler's voucher | 21 |
| Gambler's vacation destination | 34 |
| Gambler's town | 18 |
| Gambler's tormentor | 23 |
| Gambler's tactic | 20 |
| Gambler's strategy | 22 |
| Gambler's stakes | 20 |
| Gambler's stake | 19 |
| Gambler's promise, abbr. | 28 |
| Gambler's promise | 21 |
| Gambler's problem | 21 |
| Gambler's prize | 19 |
| Gambler's plunge | 20 |
| Gambler's place | 19 |
| Gambler's phrase | 20 |
| Gambler's payment | 21 |
| Gambler's pass | 18 |
| Gambler's option | 20 |
| Gambler's opening? | 22 |
| Gambler's offer | 19 |
| Gambler's obsession | 23 |
| Gambler's obligation | 24 |
| Gambler's numbers | 21 |
| Gambler's note, slangily | 28 |
| Gambler's note | 18 |
| Gambler's need | 18 |
| Gambler's moxie? | 20 |
| Gambler's money | 19 |
| Gambler's milieu | 20 |
| Gambler's method | 20 |
| Gambler's memo | 18 |
| Gambler's mecca | 19 |
| Gambler's marker | 20 |
| Gambler's mark | 18 |
| Gambler's loss? | 19 |
| Gambler's loss, figuratively | 32 |
| Gambler's last resort | 25 |
| Gambler's lament | 20 |
| Gambler's lady? | 19 |
| Gambler's jubilant cry | 26 |
| Gambler's IOU | 17 |
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