Keep repeating this method and one will end up with the same amount of money, and a maximum gambling skill in no time. However, gambling skill will still be increased since the player has 'spent' the money. When the player plays the game of roulette, the outcome is a 'no win' situation and all of the money is returned to the player. Next, half of the maximum wager should be bet on red, and half on black (e.g. They should choose the highest wager possible for their skill level.

Gambling skill can be increased without losing any money by the following method: the player must head into a casino in Las Venturas and head to a roulette table. The player can also pick up the money dropped by the gunmen to decrease their debt. The more money borrowed from the casino, the more gunmen will be sent after the player. If the player fails to repay their debt after a certain amount of time, the player will be persistently attacked by Micro SMGs and AKs-armed gunmen in a Vincent whenever they are in Las Venturas, until they repay their debt. When having -$500 or less, borrowing money puts the player in 'debt', resulting in the player receiving phone calls from the loaner about returning their money once the player leaves a casino. The amount allowed to borrow in each round at the table is based in how high the gambling skill is the higher the skill the more is allowed to borrow. When the player runs out of money (having $0), the player can borrow money from the casino when playing at a casino table (an amount of borrowed money corresponds with the player's wager on the table), leading to a negative money value.

There are certain activities that bar the player from playing due to a low gambling skill, such as the Wheel of Fortune, which only allows those who could at least wager a maximum of $10,000. The skill increases by 1 for every $1,000 spent up to a maximum skill of 1000. In GTA San Andreas, the player can increase the gambling skill of Carl Johnson by spending money at the casinos.

With its expansion in GTA San Andreas the chances of losing/winning are more probable. In Grand Theft Auto: San Andreas, more activities were available that the player can take part in to wager money on in order to gain more money if the player wins the activity or lose the money wagered if the player loses the activity. The ability to wager money is first introduced in Grand Theft Auto: Vice City, when the player must pay entrance fees for Vice Street Racer events, with a set limit on how much they can bet, and perform well enough in the races to break even.

Ranking odds on casino games