Bronze:

Viva la Resistenza!
Objective: Complete Chapter 1.

Home Sweet Home
Objective: Complete Chapter 2.

Back in Business
Objective: Do your first job for Mike Bruski.

Big Brother
Objective: Protect Francesca.

A Real Gentleman
Objective: Help the woman fix her car in Home Sweet Home.

The Price of Oil
Objective: Complete Chapter 3.

The Professional
Objective: Obtain the ration stamps without raising the alarm.

Mail Man
Objective: Sell all the gas stamps before the time runs out.

Night Shift
Objective: Complete Chapter 4.

Good Spirits
Objective: Complete Chapter 5.

Time Well Spent
Objective: Complete Chapter 6.

Last Respects
Objective: Complete Chapter 7.

The Wild Ones
Objective: Complete Chapter 8.

Man of Honor
Objective: Complete Chapter 9.

Checking Out
Objective: Complete Chapter 10.

Our Good Friend
Objective: Complete Chapter 11.

Wake Up Call
Objective: Help Leo out of a tricky situation without getting caught.

Chasing the Dragon
Objective: Complete Chapter 12.

Chop Chop!
Objective: Complete Chapter 13.

Get Rich or Die Flyin'
Objective: Get all wheels of your car into the air for at least 20 meters and then touch the ground again.

Pedal to the Metal
Objective: Travel at 125 mph.

One Careful Owner
Objective: Travel a total of 50 miles in one vehicle.

Proper Scapper
Objective: Sell 5 vehicles to Mike Bruski at the scrapyard.

Exporter
Objective: Sell 5 vehicles to Derek at the dock.

Cruise Control
Objective: Keep any vehicle at 30 mph or over for 5 or more minutes.

Hairdresser
Objective: Kill 5 enemies in rapid succession with a headshot.

Knucklehead
Objective: Kill a total of 30 enemies using melee attacks.

Stuck Up
Objective: Rob 5 stores in under 5 minutes.

The Enforcer
Objective: Kill 50 enemies.

Sharp Suiter
Objective: Buy your first luxury suit.

Tuned Ride
Objective: Upgrade one of your cars one level.

Dream Handling
Objective: Upgrade one of your cars to the maximum level.

Hard to Kill
Objective: The police want you dead. Survive for 10 minutes!

Collector's Item
Objective: Find at least one collectible in the game.

Petrol Head
Objective: Drive at least 30 different vehicles.

Silver:

Met at Work
Objective: Complete Chapter 14.

Finish Him
Objective: Finish what you started.

Ladies' Man
Objective: Find all of the Playboy magazines.

Card Sharp
Objective: Find all of the Wanted posters.