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