| 1 | Introduction | — | Portland | — |
| 2 | Give Me Liberty | 8-Ball | Portland | — |
| 3 | Luigi's Girls | Luigi Goterelli | Portland | $1,500 and the Portland safehouse |
| 4 | Don't Spank Ma Bitch Up | Luigi Goterelli | Portland | $4,000 |
| 5 | Drive Misty For Me | Luigi Goterelli | Portland | $1,000 |
| 6 | Pump-Action Pimp | Luigi Goterelli | Portland | $4,000, plus the Pistol stocked at Ammu-Nation |
| 7 | The Fuzz Ball | Luigi Goterelli | Portland | $2,000 for the required four girls, plus $500 for each extra girl up to $4,000 |
| 8 | Mike Lips Last Lunch | Joey Leone | Portland | $10,000 |
| 9 | Farewell 'Chunky' Lee Chong | Joey Leone | Portland | $10,000, plus the Pistol stocked at Ammu-Nation |
| 10 | Van Heist | Joey Leone | Portland | $20,000 |
| 11 | Cipriani's Chauffeur | Joey Leone | Portland | $3,000, with $2,000 more for killing every Triad in the ambush, plus the Uzi stocked at Ammu-Nation |
| 12 | Dead Skunk in the Trunk | Joey Leone | Portland | $10,000 |
| 13 | The Getaway | Joey Leone | Portland | $10,000 per surviving robber, up to $30,000 |
| 14 | Taking Out the Laundry | Toni Cipriani | Portland | $20,000 |
| 15 | The Pick-Up | Toni Cipriani | Portland | $10,000 |
| 16 | Salvatore's Called a Meeting | Toni Cipriani | Portland | $15,000 |
| 17 | Chaperone | Salvatore Leone | Portland | $10,000 |
| 18 | Triads and Tribulations | Toni Cipriani | Portland | $30,000 |
| 19 | Blow Fish | Toni Cipriani | Portland | $30,000 |
| 20 | Cutting the Grass | Salvatore Leone | Portland | $15,000 |
| 21 | Bomb Da Base: Act I | Salvatore Leone | Portland | — |
| 22 | Bomb Da Base: Act II | 8-Ball | Portland | $150,000 |
| 23 | Last Requests | Salvatore Leone | Portland | $20,000, access to Staunton Island and the Staunton Island safehouse |
| 24 | The Crook | Marty Chonks | Portland | $1,000 |
| 25 | The Thieves | Marty Chonks | Portland | $2,000 |
| 26 | The Wife | Marty Chonks | Portland | $3,000 |
| 27 | Her Lover | Marty Chonks | Portland | $4,000 |
| 28 | Turismo | El Burro | Portland | $10,000 |
| 29 | I Scream, You Scream | El Burro | Portland | $8,000 |
| 30 | Trial By Fire | El Burro | Portland | $10,000 |
| 31 | Big'n'Veiny | El Burro | Portland | $20,000 |
| 32 | Sayonara Salvatore | Asuka Kasen | Staunton Island | $25,000 |
| 33 | Under Surveillance | Asuka Kasen | Staunton Island | $15,000 |
| 34 | Paparazzi Purge | Asuka Kasen | Staunton Island | $10,000 |
| 35 | Payday For Ray | Asuka Kasen | Staunton Island | $11,000 |
| 36 | Two-Faced Tanner | Asuka Kasen | Staunton Island | $20,000 |
| 37 | Kanbu Bust-out | Kenji Kasen | Staunton Island | $30,000 |
| 38 | Grand Theft Auto | Kenji Kasen | Staunton Island | $25,000 |
| 39 | Deal Steal | Kenji Kasen | Staunton Island | $25,000 |
| 40 | Shima | Kenji Kasen | Staunton Island | $10,000 |
| 41 | Smack Down | Kenji Kasen | Staunton Island | $10,000, plus $1,000 for each dealer killed beyond the eighth |
| 42 | Silence the Sneak | Ray Machowski | Staunton Island | $30,000 |
| 43 | Arms Shortage | Ray Machowski | Staunton Island | $10,000 and access to Phil's Army Surplus |
| 44 | Evidence Dash | Ray Machowski | Staunton Island | $10,000 |
| 45 | Gone Fishing | Ray Machowski | Staunton Island | $15,000 |
| 46 | Plaster Blaster | Ray Machowski | Staunton Island | $10,000 |
| 47 | Liberator | Donald Love | Staunton Island | $40,000 |
| 48 | Waka-Gashira Wipeout! | Donald Love | Staunton Island | $30,000 |
| 49 | A Drop in the Ocean | Donald Love | Staunton Island | $10,000, access to Shoreside Vale and the Shoreside Vale safehouse |
| 50 | Grand Theft Aero | Donald Love | Staunton Island | $50,000 |
| 51 | Escort Service | Donald Love | Staunton Island | $40,000 |
| 52 | Decoy | Donald Love | Staunton Island | $35,000 |
| 53 | Love's Disappearance | Donald Love | Staunton Island | — |
| 54 | Marked Man | Ray Machowski | Staunton Island | $20,000, a bullet-proof Patriot and a stash of Sniper Rifle, M16, Rocket Launcher and Flamethrower |
| 55 | Bait | Asuka Kasen | Staunton Island | $35,000 |
| 56 | Espresso-2-Go! | Asuka Kasen | Staunton Island | $40,000 |
| 57 | S.A.M. | Asuka Kasen | Staunton Island | $45,000 |
| 58 | Ransom | Catalina | Staunton Island | — |
| 59 | Bling-bling Scramble | King Courtney | Staunton Island | Up to $15,000, at $1,000 per checkpoint collected |
| 60 | Uzi Rider | King Courtney | Staunton Island | $10,000 |
| 61 | Gangcar Round-up | King Courtney | Staunton Island | $10,000 |
| 62 | Kingdom Come | King Courtney | Staunton Island | $10,000 |
| 63 | Uzi Money | D-Ice | Shoreside Vale | $10,000 |
| 64 | Toyminator | D-Ice | Shoreside Vale | $10,000 |
| 65 | Rigged to Blow | D-Ice | Shoreside Vale | $20,000 |
| 66 | Bullion Run | D-Ice | Shoreside Vale | $25,000 |
| 67 | Rumble | D-Ice | Shoreside Vale | $10,000 |
| 68 | The Exchange | Catalina | Shoreside Vale | $1,000,000 and a Rhino at Phil's Army Surplus |