| Trophy | How to unlock
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| A Dog, a Whale and a Clock Walks Into a Hole… (Silver) | Allow Bob to be woken by a dog, an alarm clock, a whale train and a manhole.
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| Back to Bed (Bronze) | Get Bob safely to the end of the last level.
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| Checkmate (Silver) | Scare five chess pieces.
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| Deeper Into the Dream (Bronze) | Help Bob through the first dream world.
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| Déjà vu (Bronze) | Complete the first dream world in nightmare mode.
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| Groundhog Night (Bronze) | Make Bob walk over the edge 10 times in a single level.
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| Grown Attached (Bronze) | Spend 10 minutes in one level.
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| If at First You Don't Succeed (Bronze) | Retry a single level 5 times.
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| Just Five More Minutes (Silver) | Send 10 wheel clocks over the edge.
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| No Time to Explain! (Bronze) | Skip five cut scenes.
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| Now You are Thinking With… (Bronze) | Walk through portals 30 times.
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| Open Sesame (Bronze) | Open a door in nightmare mode.
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| So Much Easier the First Time (Bronze) | Complete the game in nightmare mode.
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| Speed Runner (Silver) | Complete levels 1 - 30 in under 45 minutes.
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| The Button is Stuck! (Bronze) | Use the fast forward function for a combined 5 minutes.
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| Understanding the Basics (Bronze) | Complete the first 3 levels to learn the basics of the game.
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