| 1. |  Blitz | Windward - Ep. 1 - The Valiant! - Let's Play | 84 | Let's Play |
| 2. | Blitz | Windward - Ep. 2 - Raise the Blue Sails! - Let's Play | 47 | Let's Play |
| 3. | Yippee Ki Yay Mr Falcon | Falcon 1 Shot - Let's Play Windward - Yarr Pirates! - Gameplay Impressions | 30 | Let's Play |
| 4. | Blitz | Windward - Ep. 7 - Thunder Rolls! - Let's Play | 21 | Let's Play |
| 5. | Blitz | Windward - Ep. 3 - The Deadly Reef! - Let's Play | 21 | Let's Play |
| 6. | GloryHoundd | Windward playthrough! | 20 | Let's Play |
| 7. | Blitz | Windward - Ep. 13 - More Server Play! - Let's Play | 20 | Let's Play |
| 8. | Blitz | Windward - Ep. 11 - Testing Online Waters! - Let's Play | 20 | Let's Play |
| 9. | Blitz | Windward - Ep. 6 - The Stealth Mission! - Let's Play | 17 | Let's Play |
| 10. | Blitz | Windward - Ep. 8 - Gaining A Foothold! - Let's Play | 16 | Let's Play |
| 11. | Blitz | Windward - Ep. 15 - The Final Battle - Let's Play | 16 | Let's Play |
| 12. | Blitz | Windward - Ep. 12 - Rocking an Instance! - Let's Play | 14 | Let's Play |
| 13. | Blitz | Windward - Ep. 5 - Circling Like Sharks! - Let's Play | 14 | Let's Play |
| 14. | Blitz | Windward - Ep. 9 - Farming Some Quests! - Let's Play | 13 | Let's Play |
| 15. | Blitz | Windward - Ep. 10 - Poison Fog! - Let's Play | 10 | Let's Play |
| 16. | Blitz | Windward - Ep. 14 - Ship of the Line! - Let's Play | 10 | Let's Play |
| 17. | DieselDesigns Gaming | Let's Play Windward: EP07: Pirate Captain Boss! WAR Part 2 (Early Access Let's Play 60FPS) | 9 | Let's Play |
| 18. | DieselDesigns Gaming | Let's Play Windward: EP13: #WarWeek Death Follow Us All! Part 3 (Let's Play 60FPS) | 9 | Let's Play |
| 19. | DieselDesigns Gaming | Let's Play Windward: EP06: Royal Brigantine & Pirate WAR! Part.1 (Early Access Let's Play 60FPS) | 8 | Let's Play |
| 20. | Blitz | Windward - Ep. 4 - Tactical Retreat! - Let's Play | 7 | Let's Play |
| 21. | OneLastMidnight | WINDWARD - PART 1 - STARTING OUT - Let's Play / Gameplay | 7 | Let's Play |
| 22. | DieselDesigns Gaming | Let's Play Windward: EP08: Making Gold! (Early Access Let's Play 60FPS) | 6 | Let's Play |
| 23. | It's Jackson | Windward Let's Play EP05 | ONLINE TASHAREN EAST COAST 1 | 5 | Let's Play |
| 24. | DieselDesigns Gaming | Windward: EP01: Getting My Sea Legs! (Early Access Let's Play 60FPS) | 5 | Let's Play |
| 25. | Welsknight Gaming | Let's Play Windward - Ep. 1: Totally Not Sid Meier's Pirates! | Windward Gameplay/Walkthrough | 4 | Let's Play |
| 26. | Welsknight Gaming | Let's Play Windward - Ep. 2: Schooner vs. Pirates! | Windward Gameplay/Walkthrough | 4 | Let's Play |
| 27. | DieselDesigns Gaming | Let's Play Windward: EP18: Level 24 Pirate Area! (Let's Play 60FPS) | 4 | Let's Play |
| 28. | DieselDesigns Gaming | Let's Play Windward: EP20: Conquering the West! (Let's Play 60FPS) | 4 | Let's Play |
| 29. | DieselDesigns Gaming | Let's Play Windward: EP14: #WarWeek Double-Tap Fire BOMB! Part 3 (Let's Play 60FPS) | 4 | Let's Play |
| 30. | OneLastMidnight | Windward - Part 2 - Battle!!! - Let's Play / Gameplay | 4 | Let's Play |
| 31. | DieselDesigns Gaming | Let's Play Windward: EP04: WAR! Part.1 (Early Access 60FPS) | 3 | Let's Play |
| 32. | DieselDesigns Gaming | Let's Play Windward: EP11: War Week! Part 1 (Let's Play 60FPS) | 3 | Let's Play |
| 33. | DieselDesigns Gaming | Let's Play Windward: EP22: Finale with a FaceCam! (60FPS) | 3 | Let's Play |
| 34. | DieselDesigns Gaming | Let's Play Windward: EP05: WAR!!! Part 2 (Early Access Let's Play 60FPS) | 3 | Let's Play |
| 35. | It's Jackson | Windward Let's Play EP07 | The New and Improved Server! | 3 | Let's Play |
| 36. | It's Jackson | Windward Let's Play EP06 | What Pirates? | 3 | Let's Play |
| 37. | It's Jackson | Windward Let's Play EP03 | COMBAT INSTANCE! | 3 | Let's Play |
| 38. | DieselDesigns Gaming | Let's Play Windward: EP21: New Ship, the Corvette! (Let's Play 60FPS) | 3 | Let's Play |
| 39. | DieselDesigns Gaming | Let's Play Windward: EP15: #WarWeek New Ship The Frigate! (Let's Play 60FPS) | 2 | Let's Play |
| 40. | OneLastMidnight | Windward Gameplay - UGH, THE PIRATE SLIDER! WHO KNEW?!? - Part 14 - Lets Play Windward | 2 | Let's Play |
| 41. | It's Jackson | Windward Let's Play EP01 | The Sojourn Faction | 2 | Let's Play |
| 42. | It's Jackson | Windward Let's Play EP02 | BYE BYE PIRATES! | 2 | Let's Play |
| 43. | DieselDesigns Gaming | Let's Play Windward: EP09: Leader of the Armada! Part 1 (Early Access Let's Play 60FPS) | 2 | Let's Play |
| 44. | DieselDesigns Gaming | Let's Play Windward: EP12: #WarWeek POISONED! Part 2 (Let's Play 60FPS) | 2 | Let's Play |
| 45. | DieselDesigns Gaming | Let's Play Windward: EP10: Armada Destruction! Part 2 (Early Access Let's Play 60FPS) | 2 | Let's Play |
| 46. | DieselDesigns Gaming | Let's Play Windward: EP19: Pirate Captains and Destruction! (Let's Play 60FPS) | 1 | Let's Play |
| 47. | Welsknight Gaming | Let's Play Windward - Ep. 4: The Brigantine | Windward Gameplay/Walkthrough | 1 | Let's Play |
| 48. | InsertValue | Let's Play WINDWARD Deutsch Teil 1 Segel Setzen / WINDWARD PC Gameplay German 1440p 60fps | 1 | Let's Play |
| 49. | DieselDesigns Gaming | Let's Play Windward: EP16: #WarWeek Level 15 Area! (Let's Play 60FPS) | 1 | Let's Play |
| 50. | Rampancy | Let's Play Windward | 1 | Let's Play |
| 51. | Welsknight Gaming | Let's Play Windward - Ep. 3: Recruiting Allies | Windward Gameplay/Walkthrough | 1 | Let's Play |
| 52. | DieselDesigns Gaming | Let's Play Windward: EP17: #WarWeek Pirate Instance?!!! (Let's Play 60FPS) | 1 | Let's Play |
| 53. | DieselDesigns Gaming | Let's Play Windward: EP03: New Warship & New Area! (Early Access 60FPS) | 1 | Let's Play |
| 54. | Welsknight Gaming | Let's Play Windward - Ep. 5: The Last Stand | Windward Gameplay/Walkthrough | 1 | Let's Play |
