by Malcadon » November 18th, 2025, 5:22 pm
If you are going by 5e rules, you can make an ability check based on whet the character is doing. If this is a game of cards or dice, or even a setup like chess, billiards or roulette, this would require a Tool Proficiency in the equivalent Game Set. When playing with others, you can make a Wisdom (Insight) check to read faces at card games, a Wisdom (Perception) check to spot cheating or to "count" or "read" cards, a Charisma (Deception) check to bluff, a Dexterity (Slight-at-Hand) check to cheat. Sports Betting, there you wager on the outcome of a game, is an Insight Check to see who has the best odds for winning -- this will not guarantee a win. In most cases, these checks would have a DC 15.
In the 1e AD&D Dungeon Master Guide, there are a list of games for gambling, including the rules to a number of games in Appendix F: Gambling on page 215. They are variations of card, dice and slot machine games (the slot machine games are expressed by rolling three dice in order, with each number being a fruit, BAR and other icons.) This was included so, at the DM's discretion, players could play the game as part of the role-play. In practice, this greatly slowed down the game and players who are not gambling have nothing to do. But, they are good reads.
I have seen a series of old '70s third-party fantasy RPG supplements and adventures that were made for D&D, but legal treats force the company to used a "Universal" metric to make their content usable for multiple game systems. Part of this metric is to include twice the normal number of abilities (to a redundant degree) including a stat for Gambling. This is used to make ability checks in order to win at games and betting. In some of their setting booklets, establishments that have gambling (taverns, gambling dens, brothels, etc.) would list adjustments to account for "house odds" (although, the real gamble in the places listed is not getting bed lice or you pockets pinched). Mind you, this well before Skills (or Non-Weapon Proficiencies) where a thing, and Ability Checks amounted to rolling at or under your ability score with a d20.
All-and-all, your best bet is to use the 5e approach with ability (skill) checks. You can make a single check for a evening of dice or cards with tavern regulars, or an elaborate series of checks while facing off with a serious high stakes gambler. You can up the DC by the house odds of an establishment or the proficiency of a skilled player.