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Win a game of pool.
Pool can be played at numerous locations around the game, predominately at bars.
There is no pool icon on the minimap, and bars are not represented either.
However, the Ten Green Bottles bar is conveniently located on Grove Street and you can access it from the very beginning of the game.
Once inside the bar, walk up to the pool table and press (triangle) to begin a game against the CPU opponent.
Pool functions like it does in any other video game, you must sink all the strips or solid balls and then the 8-ball before your opponent.
The skill level of your opponent can vary drastically between games.
Sometimes they dont ever miss a shot, and then other times they sink the 8-ball early on in the match which means you automatically win.
Just keep playing until you eventually beat him, you can set a wager before the match, with the minimum being $50.

The below video shows the location of the Ten Green Bottles bar, as well as me beating the opponent and unlocking the trophy: