| 2026-02-16 |  Miles The Man | 1,720 | Yar har fiddle dee dee, being a pirate is alright with me! | Sid Meier's Pirates | 0:00 |
| 2025-11-25 | Classic Game Sessions | 4,730 | Sid Meier's Railroad Tycoon - longplay fullplay - MicroProse, 1990 - PC / DOS - railroad strategy | 0:00 |
| 2025-10-29 | AndySlaps | 11,400 | I played a DEAD Pirate game 20 years later and it’s Amazing | 0:00 |
| 2025-09-08 | Tong Zou | 4,059 | Let's play Sid Meier's Pirates! (2007, PSP) | 0:00 |
| 2025-04-11 | skatemancory222 | 1,130 | Sid Meier's Pirates! (NES) - Any% - 2.750 (165 frames) | 0:00 |
| 2024-12-03 | Mot2332 | 690 | (Sid Meier's Pirates!) The Greatest Pirate Game | 0:00 |
| 2024-03-31 | Papa Pete | 7,790 | Sid Meier's Pirates: Live the Life - Papa Pete's Xbox OG Library #xboxog #xbox | 0:23 |
| 2023-07-24 | Pixelmusement | 24,800 | Sid Meier's Pirates! - NNRG Week 7 | 24:21 |
| 2022-06-23 | My Bourbon is Older than Your Teammate | 10 | My Bourbon is Older than Your Teammate: Episode 2 - Remake! Please!? | 1:03:30 |
| 2022-01-01 | Gaming Jay | 7,840 | Sid Meier's Pirates! (Xbox) (Part 3) - Saturday Afternoon Gaming | 0:00 |
| 2021-12-27 | Loonsloon | 4,420 | Loonsloon HOLIDAY Wildcard Livestream 2021 | Sid Meier's Pirates! (2005 release) | Swashbuckler | 2:58:27 |
| 2021-06-28 | Midweek Ch | 148 | The Sloop 3 sails on! In Sid Meier's Pirates | 1:05:55 |
| 2020-11-29 | mrJuck Clips | 19 | deez names - Sid Meier's Pirates! | 0:51 |
| 2020-09-21 | ArchivesGameCubeTrailers | 837 | Sid Meier's Pirates! - E3 2005 - Gameplay | 1:23 |
| 2020-05-29 | Nonsonic | 780 | Xbox One Live Stream Sid Meier's Pirates - Original Xbox game | 26:51 |
| 2019-12-10 | BastichB 64K | 22,500 | Sid Meier's Pirates! (Commodore 64) Review | 3:01 |
| 2019-09-18 | Liana K | 25,700 | A Completely Accidental Example Of Why Free Speech Is Awesome! | 4:25 |
| 2019-05-11 | Vintage Arcade377 | 548 | Sid Meier's ~ Pirates! gameplay | 46:27 |
| 2019-02-23 | Sirdeathvids | 6,330 | The Fleet | Sid Meier's Pirates Part 2 | 17:33 |
| 2018-10-11 | Handheld Junkie | 1,480 | 🔴Sid Myers Pirates - PSP REVIEW🔧 | 7:21 |
| 2018-08-24 | The New Retro Show | 9,060 | Atari games on Apple II E | 23:26 |
| 2018-03-22 | mrJuck | 45 | It's the Pirate's Life for Me - Sid Meier's Pirates! Pt. 1 | 3:21:48 |
| 2017-09-04 | RetroChaoz | 52 | Rétro Chaos #3 - Pirates! (NES) | 42:38 |
| 2016-11-17 | AwfulTerrible | 116 | Sid Meier's Pirates! - Part 2: The Buccaneer Christian Apollo - Mutiny Week! | 18:19 |
| 2016-08-01 | Tsunscreen | 24,200 | Sid Meier's Pirates! - Town - Merchant 8 | 0:34 |
| 2015-05-26 | Old World Gamer | 1,150 | Pirates S1E12 - Relaxing Day on the Sea | 16:44 |
| 2015-05-18 | BlueAnkylo | 12,200 | 2-13. Let's Livestream Sid Meier's Pirates! | 54:12 |
| 2015-04-10 | Aramazon | 875 | Let's Play Sid Meier's Pirates! - Embarrassing! (2) | 43:44 |
| 2015-02-24 | MacGhriogair | 16,700 | Let's Play Caribbean! Season 3 Episode 1: Ship Ahoy! | 26:49 |
| 2012-07-20 | Mah-Dry-Bread | 418,000 | Let's Stream Sid Meier's Pirates! with Mah-Dry-Bread | 1:23:56 |
| 2012-06-05 | GingerSwitch | 958 | Let's Play: King's Bounty (GEN) | 20:22 |
| 2012-04-22 | Del | 6,840 | SID MEIERS PIRATES! FOR IOS | 4:14 |
| 2011-06-10 | Gamer's Intuition | 1,200 | Wii U Pirates | 0:12 |
| 2010-05-26 | riotctrl | 99 | Take that Henry Morgan - Pirates | 1:18 |
