| Playmate 1 | Chapter 2 "Follow Joe to his Garage" | On Joe's coffee table |
| Playmate 3 | Chapter 2 "Car Crusher" | On shelf in three-car garage |
| Playmate 18 | Chapter 3 "The Southport Docks" | On floor outside Derek's office |
| Playmate 4 | Chapter 3 "Drive to Maria Angello's" | On the floor of Maria's apartment behind the door |
| Playmate 5 | Chapter 3 "Get Inside the Office" | In the Industrial Specialists Office on the windowsill |
| Playmate 40 | Chapter 3 "Get Inside the Office" | On the first floor security guard desk |
| Playmate 6 | Chapter 3 "Get Inside the Office" | On the floor of the basement stoarage room |
| Playmate 9 | Chapter 4 "Get Out of the Mall" | In a box on the first stairwell landing |
| Playmate 2 | Chapter 4 "Get Out of the Mall" | By locked doors in the 2nd stairwell after the bookstore |
| Playmate 8 | Chapter 4 "Fend off the Cops" | On floor of the rooftop structure |
| Playmate 7 | Chapter 4 "Go to Sleep" | At the bottom of the stairs (do not go into the apartment) |
| Playmate 11 | Chapter 5 "Kill the Fat Man" | Exit the apartment with Henry and Joe and take the stairs up |
| Playmate 10 | Chapter 5 "Kill the Fat Man" | Quickly get to the first floor distillery office, it is on a shelf |
| Playmate 12 | Chapter 5 "Kill the Fat Man" | On the 5th floor, look to the right as you escort Henry |
| Playmate 13 | Chapter 6 "Contact Leo Galante" | Under the sleeping prisoner |
| Playmate 14 | Chapter 6 "Contact Leo Galante" | Search behind the grey shack by the basketball court |
| Playmate 15 | Chapter 6 "Go to the Guard" | On top of the large drying machine |
| Playmate 16 | Chapter 7 "Playmate 16" | Catch Up with Joe-On the floor of the gun store near the stairs |
| Playmate 50 | Chapter 7 "Drive with Joe to Apartment" | At the end of the hall on the top floor |
| Playmate 17 | Chapter 7 "Drive with Joe to Apartment" | On the hallway table on the 2nd floor |
| Playmate 46 | Chapter 7 "Drive with Joe to Apartment" | On the kitchen table in the apartment |
| Playmate 19 | Chapter 8 "Take Out the Greasers" | In a shack around the corner in the foundry |
| Playmate 21 | Chapter 8 "Take Out the Greasers" | On the ground near some oil drums |
| Playmate 20 | Chapter 8 "Take Out the Greasers" | Search the narrow alley to the left of the mob, it is in a shack |
| Playmate 41 | Chapter 9 "Head to Maltese Falcon" | Lying on the bar |
| Playmate 23 | Chapter 9 "Find Way into Slaughterhouse" | Search the tunnel to the left of the sewage dump |
| Playmate 22 | Chapter 9 "Slaughterhouse Interior" | On the floor in the first slaughterhouse area |
| Playmate 24 | Chapter 9 "Save Your Guys" | On a shelf in the back corner near the entrance |
| Playmate 25 | Chapter 10 "Find Cleaners Uniform" | On a desk in an office in the rear of a laundry area |
| Playmate 27 | Chapter 10 "Follow Joe to Roof" | On the floor downstairs -- do not follow Joe upstairs |
| Playmate 26 | Chapter 10 "Find Window Washing Platform" | On the floor by the elevator power source |
| Playmate 48 | Chapter 11 "Get the Door" | On the bathroom floor |
| Playmate 47 | Chapter 11 "Drive Leo to Train Station" | Search the 2nd floor of the house, it is on a window sill in the hallway |
| Playmate 29 | Chapter 11 "Drive Leo to Train Station" | Search the 2nd floor of the house, it is in the bathroom |
| Playmate 28 | Chapter 11 "Go Home" | On the bedroom floor |
| Playmate 49 | Chapter 11 "You Must Get Dressed" | On the floor by Joe's bed |
| Playmate 30 | Chapter 11 "Catch Irish Leader" | Under a box in the end of the hallway |
| Playmate 32 | Chapter 12 "Drive to Seagift Warehouse" | Between the delivery truck and the crates |
| Playmate 31 | Chapter 12 "Drive to Seagift Warehouse" | In an alley behind some dumpsters |
| Playmate 33 | Chapter 12 "Get Out of Here!" | Under the green power panel on the wall |
| Playmate 34 | Chapter 13 "Find Wong" | In the rear corner of the main dining area |
| Playmate 36 | Chapter 13 "Find Wong" | In the opium den, on a wooden crate |
| Playmate 35 | Chapter 13 "Find Wong, Basement" | In the basement of the armory on a box |
| Playmate 44 | Chapter 14 "Get Out of the Building with Joe" | Search the narrow area on the eastern edge of the building |
| Playmate 37 | Chapter 14 "Floor 3" | On a stack of burning pallets |
| Playmate 38 | Chapter 14 "Floor 3" | In the rear corner of the room with a single shooter |
| Playmate 45 | Chapter 15 "Observatory" | In the first floor stairwell |
| Playmate 39 | Chapter 15 "Observatory Roof" | Search the western edge of the roof |
| Playmate 43 | Chapter 15 "Observatory Interior" | Behind the telescope, staircase |
| Playmate 42 | Chapter 15 "Leave the Observatory" | At the base of the observatory projector |
| A Lesson in Manners (Silver) | Show that you know how to treat a lady |
| A Real Gentleman (Bronze) | Help the woman fix her car in Home Sweet Home |
| Back in Business (Bronze) | Do your first job for Mike Bruski |
| Big Brother (Bronze) | Protect Francesca |
| Card Sharp (Silver) | Find all of the Wanted posters |
| Chasing the Dragon (Bronze) | Complete Chapter 12 |
| Checking Out (Bronze) | Complete Chapter 10 |
| Chop Chop! (Bronze) | Complete Chapter 13 |
| Collector's Item (Bronze) | Find at least one collectible in the game |
| Cruise Control (Bronze) | Keep any vehicle at 30 mph or over for 5 or more minutes |
| Dream Handling (Bronze) | Upgrade one of your cars to the maximum level |
| End of the Rainbow (Silver) | Settle the score with the Irish once and for all |
| Exporter (Bronze) | Sell 5 vehicles to Derek at the dock |
| Finish Him (Silver) | Finish what you started |
| Get Rich or Die Flyin' (Bronze) | Get all wheels of your car into the air for at least 20 meters and then touch the ground again |
| Good Spirits (Bronze) | Complete Chapter 5 |
| Hairdresser (Bronze) | Kill 5 enemies in rapid succession with a headshot |
| Hard to Kill (Bronze) | The police want you dead, Survive for 10 minutes! |
| He Who Pays the Barber (Silver) | Improve the dockworker's haircuts |
| Hey Joe (Silver) | Clean up after Joe |
| Home Sweet Home (Bronze) | Complete Chapter 2 |
| Knucklehead (Bronze) | Kill a total of 30 enemies using melee attacks |
| Ladies' Man (Silver) | Find all of the Playboy magazines |
| Last Respects (Bronze) | Complete Chapter 7 |
| Made Man (Gold) | Finish the story on Medium difficulty or higher |
| Mail Man (Bronze) | Sell all the gas stamps before the time runs out |
| Man of Honor (Bronze) | Complete Chapter 9 |
| Met at Work (Silver) | Complete Chapter 14 |
| Night Shift (Bronze) | Complete Chapter 4 |
| One Careful Owner (Bronze) | Travel a total of 50 miles in one vehicle |
| Our Good Friend (Bronze) | Complete Chapter 11 |
| Out for Justice (Silver) | Learn what it means to be a Scaletta |
| Pedal to the Metal (Bronze) | Travel at 125 mph |
| Petrol Head (Bronze) | Drive at least 30 different vehicles |
| Proper Scapper (Bronze) | Sell 5 vehicles to Mike Bruski at the scrapyard |
| Sharp Suiter (Bronze) | Buy your first luxury suit |
| Stuck Up (Bronze) | Rob 5 stores in under 5 minutes |
| The Enforcer (Bronze) | Kill 50 enemies |
| The Mafia Never Forgets (Silver) | Pay a visit to an old friend |
| The Price of Oil (Bronze) | Complete Chapter 3 |
| The Professional (Bronze) | Obtain the ration stamps without raising the alarm |
| The Wild Ones (Bronze) | Complete Chapter 8 |
| Time Well Spent (Bronze) | Complete Chapter 6 |
| Tough Nut (Gold) | Finish the story on Hard difficulty level |
| Tuned Ride (Bronze) | Upgrade one of your cars one level |
| Viva la Resistenza! (Bronze) | Complete Chapter 1 |
| Wake Up Call (Bronze) | Help Leo out of a tricky situation without getting caught |
| Platinum Trophy (Platinum) | Unlocked when all trophies collected |
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