| 1. |  The Spiffing Brit | SID MEIERS PIRATES IS A PERFECTLY BALANCED GAME WITH NO EXPLOITS - Boarding only challenge IS BROKEN | 5,080 | |
| 2. | Sips | An Evening With Sips - Sid Meier's Pirates! | 2,086 | |
| 3. | Sips | Salty Dogs (Sips Plays Sid Meier's Pirates! - Part 3) | 594 | |
| 4. | Sips | Alandin's Quest (Sips Plays Sid Meier's Pirates! - Part 1) | 518 | |
| 5. | Sips | Switching Sides (Sips Plays Sid Meier's Pirates! - Part 6) | 493 | |
| 6. | Sips | Forced Retirement (Sips Plays Sid Meier's Pirates! - FINALE) | 487 | |
| 7. | Sips | Disaster Strikes (Sips Plays Sid Meier's Pirates! - Part 4) | 471 | |
| 8. | Sips | The Big Time (Sips Plays Sid Meier's Pirates! - Part 5) | 465 | |
| 9. | Sips | Ladies Man (Sips Plays Sid Meier's Pirates! - Part 7) | 363 | |
| 10. | Sips | Delicious Revenge (Sips Plays Sid Meier's Pirates! - Part 14) | 338 | |
| 11. | Sips | Flipping Towns (Sips Plays Sid Meier's Pirates! - Part 20) | 324 | |
| 12. | Sips | Salty Battles (Sips Plays Sid Meier's Pirates! - Part 21) | 299 | |
| 13. | Sips | Secret Spice (Sips Plays Sid Meier's Pirates! - Part 28) | 297 | |
| 14. | Sips | The Sacking of Margarita (Sips Plays Sid Meier's Pirates! - Part 9) | 288 | |
| 15. | Sips | Sweet Gifts (Sips Plays Sid Meier's Pirates! - Part 13) | 284 | |
| 16. | Sips | Getting Old (Sips Plays Sid Meier's Pirates! - Part 31) | 274 | |
| 17. | Sips | Making Cheddar (Sips Plays Sid Meier's Pirates! - Part 2) | 273 | |
| 18. | Sips | Brasiliano Down (Sips Plays Sid Meier's Pirates! - Part 12) | 260 | |
| 19. | Sips | Showers of Gold (Sips Plays Sid Meier's Pirates! - Part 26) | 256 | Show |
| 20. | Sips | Salty Raymondo (Sips Plays Sid Meier's Pirates! - Part 27) | 255 | |
| 21. | Sips | Geri, Circa 1990 (Sips Plays Sid Meier's Pirates! - Part 24) | 253 | |
| 22. | Sips | Wowing Geri (Sips Plays Sid Meier's Pirates! - Part 25) | 252 | |
| 23. | Sips | Close Shaves (Sips Plays Sid Meier's Pirates! - Part 17) | 251 | |
| 24. | Sips | The Oldsmobile (Sips Plays Sid Meier's Pirates! - Part 23) | 250 | |
| 25. | Sips | Family Ties (Sips Plays Sid Meier's Pirates! - Part 19) | 249 | |
| 26. | Sips | The Setup (Sips Plays Sid Meier's Pirates! - Part 10) | 228 | |
| 27. | Sips | Hermandildo Down (Sips Plays Sid Meier's Pirates! - Part 8) | 221 | |
| 28. | Sips | Notorious (Sips Plays Sid Meier's Pirates! - Part 30) | 219 | |
| 29. | Sips | Beloved Aunt (Sips Plays Sid Meier's Pirates! - Part 29) | 210 | |
| 30. | Sips | Jailhouse Rock (Sips Plays Sid Meier's Pirates! - Part 22) | 210 | |
| 31. | Sips | Overcompensations (Sips Plays Sid Meier's Pirates! - Part 11) | 209 | |
| 32. | Sips | Everybody Loves Raymondo (Sips Plays Sid Meier's Pirates! - Part 16) | 201 | |
| 33. | Sips | Small Fortunes (Sips Plays Sid Meier's Pirates! - Part 15) | 199 | |
| 34. | Sips | Master Swordsman (Sips Plays Sid Meier's Pirates! - Part 18) | 194 | |
| 35. | Cheeky Commodore Gamer | Commodore 64 | SID MEIER's PIRATES! (1987) | 43 | |
| 36. | AL82 Retrogaming Longplays | Pirates Longplay (Arcade) [QHD] | 40 | |
| 37. | OfficiallyDevin | [TIC] Pay Rates of the Caribbean: Tales of Stingy Sal | Sid Meier's Pirates! Highlights | 36 | |
| 38. | gull payne | Sid Meier’s Pirates - PSP - Review | 24 | Review |
| 39. | Weird Wizard Dave | "Hoist the First Mate!" Wizards Eye on Tempest Gameplay | 22 | |
| 40. | OfficiallyDevin | [TIC] Pay Rates of the Caribbean | Tales of Stingy Sal #9 (Final) | Sid Meier's Pirates Highlights | 22 | |
| 41. | ZombieCleo | Pirates wedding as requested by stream | 21 | |
| 42. | Togglejam LIVE | Sid Meier's Pirates! (PC) - Somehow Still Fun! | 20 | Review |
| 43. | AVStoryteller | Sid Meier's Pirates! - Ep1 - Dread Pirate Roberts! [WebCam] Let's Play! | 20 | Let's Play |
| 44. | OfficiallyDevin | [TIC] Pay Rates of the Caribbean | Tales of Stingy Sal #8 | Sid Meier's Pirates Highlights | 19 | |
| 45. | TAPE Gaming | Sid Meier's Pirates! - Captain Spack Jarrow at Your Service! | 19 | |
| 46. | KiriothTV | BARGAIN BIN?! MORE LIKE BARGAIN WIN!! Sid Meier's Pirates! Gameplay | 17 | |
| 47. | OfficiallyDevin | [TIC] Pay Rates of the Caribbean: Tales of Stingy Sal #2 | Sid Meirs' Pirates Highlights | 17 | |
| 48. | OfficiallyDevin | [TIC] Pay Rates of the Caribbean | Tales of Stingy Sal #3 | Sid Meier's Pirates Highlights | 16 | |
| 49. | OfficiallyDevin | [TIC] Pay Rates of the Caribbean | Tales of Stingy Sal #7 | Sid Meier's Pirates Highlights | 16 | |
| 50. | Weird Wizard Dave | Man O' War Corsair - Early access gameplay Wizard Eye on... | 16 | |
| 51. | TAPE Gaming | Sid Meier's Pirates! (Part 2) - Treasure Hunting | 16 | |
| 52. | OfficiallyDevin | [TIC] Pay Rates of the Caribbean | Tales of Stingy Sal #4 | Sid Meier's Pirates Highlights | 16 | |
| 53. | OfficiallyDevin | [TIC] Pay Rates of the Caribbean | Tales of Stingy Sal #5 | Sid Meier's Pirates Highlights | 14 | |
| 54. | Lorfarius | AMIGArama Podcast Episode 50: Sid Meier's Pirates! | 11 | Show |
| 55. | AVStoryteller | Sid Meier's Pirates! - Ep26 Retirement, Careers & Fames Points [WebCam] Let's Play! | 11 | Let's Play |
| 56. | Weird Wizard Dave | Weird Wednesday - Windward - It's like Pirates... only not really. | 11 | |
| 57. | TYKE | Sid Meier's Pirates! PC play through (Part 1) | 10 | Let's Play |
| 58. | PalicoPadge | Padge Plays! Retro Edition: Sid Meier's Pirates! (2004 - Firaxis Games/Atari) 40th Birthday Special! | 10 | Let's Play |
| 59. | AVStoryteller | Sid Meier's Pirates! Ep42 Ultimate Completion! Max Fame Points! [WebCam] Let's Play! | 10 | Let's Play |
| 60. | OfficiallyDevin | [TIC] Pay Rates of the Caribbean | Tales of Stingy Sal #6 | Sid Meier's Pirates Highlights | 10 | |
| 61. | The Wandering Inn | Sheepdog's Classics, Let's Play - Sid Meier's Pirates #2 | 8 | Let's Play |
| 62. | AVStoryteller | Sid Meier's Pirates! - Ep6 - Tips and Strategies [WebCam] Let's Play! | 8 | |
| 63. | DG | Wretro Wednesdays - Sid Meier's Pirates EP3 - Long Lost SIster! | 8 | |
| 64. | AVStoryteller | Sid Meier's Pirates! - Ep15 Marquis Montalban Beat-Down! [WebCam] Let's Play! | 7 | Let's Play |
| 65. | The Wandering Inn | Sheepdog's Classics, Let's Play - Sid Meier's Pirates #6 | 7 | Let's Play |
| 66. | AVStoryteller | Sid Meier's Pirates! - Ep34 Sword Fighting the Jealous Fiance! [WebCam] Let's Play! | 7 | Let's Play |
| 67. | Kronenberg Gaming | Sid Meier's Pirates! - Game Review with Gameplay | 7 | Review |
| 68. | AVStoryteller | Sid Meier's Pirates! - Ep25 How To Get Into The Friend-Zone (With The Spanish) [WebCam] Let's Play! | 7 | Let's Play |
| 69. | The Wandering Inn | Sheepdog's Classics, Let's Play - Sid Meier's Pirates #7 | 6 | Let's Play |
| 70. | TapersCrazy | Pirates of the Caribbean: New Horizons: Ep 22: Fighting Pirates | 6 | |
| 71. | PalicoPadge | So, What Now? - Channel Update - New Series, Old Series & What To Expect Going Forward | 6 | |
| 72. | Pixel Bandits | Pixel Bandits Flashback - Sid Meier's Pirates! (2004) | 6 | |
| 73. | The Wandering Inn | Sheepdog's Classics, Let's Play - Sid Meier's Pirates #5 | 6 | Let's Play |
| 74. | The Wandering Inn | Sheepdog's Classics, Let's Play - Sid Meier's Pirates #23 | 6 | Let's Play |
| 75. | AVStoryteller | Sid Meier's Pirates! - Ep21 Defeating Marquis Montalban's Fortress & Duel! [WebCam] Let's Play! | 5 | Let's Play |
| 76. | AVStoryteller | Sid Meier's Pirates! - Ep3 - Out Run 'n Gun us!! [WebCam] Let's Play! | 5 | Let's Play |
| 77. | PalicoPadge | Buccaneers! A First Person Pirate RPG - A Bigger Gun? Cut & Run! - Buccaneers Gameplay PC Part 5 | 5 | |
| 78. | AVStoryteller | Sid Meier's Pirates! - Ep5 - Defeating Pirate Roc Brasiliano! [WebCam] Let's Play! | 5 | Let's Play |
| 79. | AVStoryteller | Sid Meier's Pirates! - Ep13 - Full Sister Map Found! [WebCam] Let's Play! | 5 | Let's Play |
| 80. | AVStoryteller | Sid Meier's Pirates! Ep41 No More Reason to Dance with Beautiful Governor's Daughters? [WebCam] | 5 | |
| 81. | AVStoryteller | Sid Meier's Pirates! - Ep2 - Smugglers, Pirates, Spanish [WebCam] Let's Play! | 5 | Let's Play |
| 82. | Lorfarius | Merchants - Psion Series 5MX | 5 | |
| 83. | IggyMaid | Locating the lost city of cheese, by accident! - Sid Meiers Pirates | 5 | |
| 84. | TapersCrazy | Pirates of the Caribbean: New Horizons: Ep 9: Troop Transport | 5 | |
| 85. | The Wandering Inn | Sheepdog's Classics, Let's Play - Sid Meier's Pirates #4 | 5 | Let's Play |
| 86. | AVStoryteller | Sid Meier's Pirates! - Ep14 Chasing Down Marquis Montalban [WebCam] Let's Play! | 5 | Let's Play |
| 87. | AVStoryteller | SM Pirates! Ep37 Returning Our Rescued Love to her Father! WEDDING TIME ! [WebCam] Let's Play! | 5 | Let's Play |
| 88. | Mallardonaise | Sid Meier's ~ Pirates: Arr I am a Pirate! | 4 | |
| 89. | DG | Wretro Wednesdays - Sid Meier's Pirates EP2 - Treasure, Treasure, Treasure! | 4 | |
| 90. | TapersCrazy | Pirates of the Caribbean: New Horizons: Ep 25: Spanish Sea Battle | 4 | |
| 91. | AVStoryteller | Sid Meier's Pirates! - Ep19 Improving Relations with Nations [WebCam] Let's Play! | 4 | Let's Play |
| 92. | The Wandering Inn | Sheepdog's Classics, Let's Play - Sid Meier's Pirates #1 | 4 | Let's Play |
| 93. | DG | Wretro Wednesdays - Sid Meier's Pirates EP4 - The Adventurer | 4 | |
| 94. | Ven's Gaming Corner | Old but Gold Games: Sid Meier's Pirates (2004) | 4 | |
| 95. | Mr Lilac | Sid Meier's Pirates! With Young Jack [Episode 4] - What The Roc Is Cookin' | 4 | Show |
| 96. | The Wandering Inn | Sheepdog's Classics, Let's Play - Sid Meier's Pirates #9 | 4 | Let's Play |
| 97. | AVStoryteller | Sid Meier's Pirates! - Ep17 Plunging Daughters [WebCam] Let's Play! | 4 | Let's Play |
| 98. | TapersCrazy | Pirates of the Caribbean: New Horizons: Ep 20: Naval Base | 4 | |
| 99. | AVStoryteller | Sid Meier's Pirates! - Ep9 - Advanced Fencing | Governer's Daughter Rewards [WebCam] Let's Play! | 4 | Let's Play |
| 100. | AVStoryteller | Sid Meier's Pirates! - Ep32 Mysterious Cities of Gold [WebCam] Let's Play! | 4 | Let's Play |
