Complete each achievement to get the allotted gamerscore. The numbers between the () is the points given for each achievement.
| Achievement | How to unlock |
| Classic Completionist (15) | Complete a full game of classic Pictionary |
| Slow Poke (10) | Fail to guess a clue before time runs out |
| Come On Already (10) | Change the clue type a lot within one round of play |
| Mind Reader (40) | Correctly guess the clue in record speed |
| Gallery Showing (10) | Create 15 Free Draw images and view them in the slideshow |
| Mega Maniac (10) | Land on 15 Mega Mania squares and correctly guess the clue |
| Blinded (20) | Guess 10 clues with the No Peeking modifier |
| Bookworm (10) | Go through each page of the tutorial |
| Brushless (40) | Guess 10 clues using nothing but the Finger Paint Tool |
| Cant Stop Wont Stop (20) | Guess 10 clues in Conveyor Belt mode |
| Challenge Accepted (20) | Guess 10 clues using mixed Draw Modes |
| Clue Master (10) | Create 20 Custom Clues |
| Committed (20) | Complete a full length 4 Team game without continuing |
| Easy Peasy (10) | Play Family Fun with Junior Clues, bonuses on, penalties off, and Picturist Chooses |
| Expert (50) | Play Family Fun with low Draw Timer, Difficult Clues, Tempus Fugit, Penalties, and Rivals Choose |
| Figure Artist (10) | Create 10 Pictionary Man drawings |
| Fun with the Family (15) | Complete a full game of Family Fun Mode |
| Guess What? (20) | Guess 10 Custom Clues |
| Hands On (20) | Guess 10 clues in Finger Painting mode |
| Handy Man (30) | Use every tool and color in one Draw Round |
| I Meant to do That (40) | Win an entire game without using the eraser or undo |
| Just Add Water (40) | Guess 10 clues using nothing but the Watercolor Tool |
| Mine, Mine, Mine! (20) | Steal a clue from another team |
| Minimalist (30) | Win a game using only one tool and one color |
| Picasso (20) | spend at least an hour on one Free Draw image |
| Picasso's Understudy (10) | Use every tool and color in one Free Draw session |
| Pictionary Maniac (15) | Complete a full game of Pictionary Mania |
| Persistent Picturist (50) | Play 50 games of Pictionary any mode |
| Pointillism (20) | Guess 10 clues in Dots Only mode |
| Prosperous Cheater (5) | Cheat through the game quickly |
| Put me in Coach! (10) | Use a customized Pictionary Man in a game |
| Quick Hitter (20) | Play Family Fun with 10 minute time limit, low Draw Timer, and Tempus Fugit |
| Resourceful (10) | Play Family Fun with Ink Limit mode, Random selections, and All Clue Categories |
| Reverse Engineer (20) | Guess 10 clues in Eraser Only mode |
| See no Evil (40) | Play Family Fun with the No Peeking modifier and the Lights Out Draw Mode |
| Shapeshifter (40) | Guess 10 clues using nothing but the Shapes Tool |
| Shutout (50) | Win every All Play square within one play session |
| Sight Beyond Sight (20) | Guess 10 clues in Lights Out mode |
| Stingy (50) | Win without letting the other team play |
| Switch Hitter (20) | Guess 10 clues with the Off Hand modifier |
| Switch! (20) | Guess 10 clues in Tool Confusion |
| Topsy Turvy (20) | Guess 10 clues in Which Way is Up mode |
| Vertigo (20) | Guess 10 clues in Rotation Frustration |
| Waste Not Want Not (20) | Guess 10 clues with the Ink Limit modifier |