 | Everybody Starts Somewhere | 10  |
| Buy your first property |
| Now You're On Your Way | 20 |
| Own your first monopoly |
| Climbing Your Way Up The Ladder | 30 |
| Build your first set of houses. Classic mode only. |
| The View From The Top | 50 |
| Build your first set of hotels. Classic mode only. |
| High Roller | 10 |
| Roll a double six |
| Rolled To Jail | 10 |
| Roll three doubles in a row and get sent to jail |
| Rolled To Freedom | 10 |
| Rolled a double to get out of jail |
| Globe Trotter | 50 |
| Land on every property on the World board |
| Taking Sides | 50 |
| Own every property, including any ports and utilities, down one whole side of the board |
| Transport King | 20 |
| Own the monopoly on the transport properties |
| You've Got The Power | 20 |
| Own the monopoly on the utilities |
| Deal Of The Century | 20 |
| Form a monopoly as a result of trading |
| No Mercy | 20 |
| Be responsible for the bankruptcy of another player |
| Went For Broke | 10 |
| Bankrupted yourself out of the game for the first time |
| A Good Start | 10 |
| Win your first mini-game in any mode of Richest |
| He Who Controls The Dice... | 50 |
| Win every mini-game in a full game of Developer |
| Last But Not Least | 20 |
| Win all the mini-games in a full game of Developer but don't finish first |
| Taken A Chance | 10 |
| Take your first property from another player using Chance in any mode of Richest |
| Forcibly Formed | 20 |
| Form a monopoly in any mode of Richest by taking one or more of the properties from another player. |
| Dashed Hopes | 10 |
| Break up another player's Monopoly |
| A Quick Victory | 10 |
| Win a game of Developer mode Richest |
| Faster Better | 20 |
| Win a game of Industrialist mode Richest |
| Becoming The Master | 40 |
| Win a game of Tycoon mode Richest |
| The Underdog | 50 |
| Don't finish first in any mini-game but still win overall in any mode of Richest |
| From The Flames | 50 |
| Come from last in the previous round to win overall in any mode of Richest |
| You Are The Richest | 100 |
| Own every property on the board in any mode of Richest |
| Started Your Empire | 30 |
| Build a set of houses in any mode of Richest |
| Established Your Hold | 50 |
| Build a set of hotels in any mode of Richest |
| Time To Collect | 10 |
| Collect your first rent payment from any other player in any mode of Richest |
| Expensive To Stop Here | 10 |
| Land on another player's set of hotels in any mode of Richest. |
| Sight Seer | 20 |
| Unlock a passport. Awarded to the passport holder |
| Jet Setter | 100 |
| Fill all the passports. Awarded to the passport holder |
| Try Something New | 10 |
| Unlock your first new board |
| The First MONOPOLY | 50 |
| Get the same amount of money as the year MONOPOLY was released |
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