Win a game of Monopoly (Default Rules)
Win a short game (Short Game - On)
Win a 4 player game against the AI (Default Rules)
Win a 4 player game without your money going below $500 (Any Rules)
Have your money dip below $100 then go on to win (Default Rules)
Win a 4 player game without buying a property outright: auctions and trading only (Default Rules)
Win a 1 vs 1 game without your opponent making a single property monopoly (Default Rules)
Win an auction (Default Rules)
Break out of jail (Default Rules)
Have two "Get Out of Jail Free" cards at the same time (Default Rules)
Complete 2 full consecutive laps of the board without paying any tax (Default Rules)
Own all railroads (Default Rules)
Own both utilities and then earn money from having a player land on one of them (Default Rules)
Own your first property monopoly (Default Rules)
Have $5000 or more in the bank (Default Rules)
Own every property, railroad and utility on one side of the board at a single time (Default Rules)
Own 5 property monopolies at any single time (Default Rules)
Buy your first house (Default Rules)
Buy your first hotel (Default Rules)
Have the bank run out of houses (Default Rules)
Receive $400 or more (at once) from landing on the Free Parking tile (Free Parking Collects Fines - On)
Receive $400 from landing on the Go tile (Landing on Go doubles your bonus - On)
Win a game with auctions turned off (Hold Auctions for Properties - Off)
Be the first to purchase a property, railroad or utility (You Must Go Round the Board Once Before Purchasing - On)
Win a 2 player game against the AI (Any Rules)
Win a 3 player game against the AI (Any Rules)
Win a 4 player game against the AI (Any Rules)