| 1. |  Blitz | 470,782 | Windward - Ep. 15 - The Final Battle - Let's Play | 32:34 |
| 2. | muyskerm | 126,320 | Too Many Pirates! | Windward Ep. 7 | 10:13 |
| 3. | GameSpot Trailers | 25,336 | Windward - Official Trailer | 1:02 |
| 4. | Noxxis Gaming | 21,676 | How To Play Windtrace 3.3 Rerun Day 1 Event Guide | Windward Arts & Hiding Spots | Genshin Impact | 11:05 |
| 5. | DieselDesigns Gaming | 16,781 | Let's Play Windward: EP22: Finale with a FaceCam! (60FPS) | 47:58 |
| 6. | Welsknight Gaming | 15,361 | Let's Play Windward - Ep. 5: The Last Stand | Windward Gameplay/Walkthrough | 24:12 |
| 7. | Gamers Nexus | 15,045 | Windward Seafaring Gameplay & Review - Editor's Choice | 8:39 |
| 8. | One Last Midnight | 11,010 | Windward - SAILS UP YE SCURVY BABOON'S! | OneLastMidnight | 1:50:41 |
| 9. | Pravus | 9,438 | Steamed! | Windward | 16:23 |
| 10. | Tantrum House | 8,727 | Windward Playthru | 48:04 |
| 11. | Quackalope | 7,912 | Windward - (Quackalope Gameplay) | 50:30 |
| 12. | Mal | 5,403 | WINDWARD | Let's Try | PC Gameplay | CO-OP w/ IDED | Part 5 | 33:38 |
| 13. | Man vs Meeple | 4,935 | Windward Preview by Man vs Meeple (El Dorado Games) | 9:20 |
| 14. | Off The Shelf Board Game Reviews | 4,046 | Windward - Full Gameplay | 1:22:18 |
| 15. | Unfiltered Gamer | 3,874 | Windward - Board Game Review | 25:27 |
| 16. | Андроид Андройдыч | 3,818 | Windward - Становимся пиратом и участвуем в морских сражениях на Android | 3:51 |
| 17. | AreYouGaming | 2,257 | Flog Plays and Reviews: Windward | 16:17 |
| 18. | Raven_2012 | 2,188 | Windward | Ep.9 | Finishing Raid Instance - Dragon Kill | 35:59 |
| 19. | Yippee Ki Yay Mr Falcon | 2,164 | Falcon 1 Shot - Let's Play Windward - Yarr Pirates! - Gameplay Impressions | 14:19 |
| 20. | MMOs.com | 2,095 | Windward Gameplay - Altay Plays | 15:02 |
| 21. | Attack Gaming | 1,741 | Windward Gameplay | First Impressions HD | 23:18 |
| 22. | Commissar BRO | 1,491 | Windward Gameplay and Impressions | 8:51 |
| 23. | GloryHoundd | 1,238 | Windward playthrough! | 1:25:11 |
| 24. | Board Game Empire | 1,117 | Windward Review - Playmonster | 11:06 |
| 25. | It's Jackson | 1,037 | Windward Let's Play EP08 | BATTLING OTHER PLAYERS! | 17:37 |
| 26. | Wolfenout Gaming | 964 | Windward| Part 8| Low on Grog as the Death Toll Rises!!! | 29:09 |
| 27. | Bay 01 | 784 | Cap'n Robobeard's Adventures in "Windward" (Part 17) | 6:49 |
| 28. | GameSpot Gameplay | 696 | Windward - Combat Specialization Gameplay Trailer | 2:20 |
| 29. | Calling All Platforms Gaming | 560 | Windward: Review | 4:29 |
| 30. | Sooo Mungry | 509 | Windward Gameplay - High Seas Pirate Battles Arrrr! - Live Stream Highlights (PC, Steam) | 13:30 |
| 31. | Uthris | 469 | Upgrades!! | Windward #2 | 17:49 |
| 32. | VGalaxy Media | 355 | Windward Review and Gameplay | 2:14 |
| 33. | nekobun | 321 | Bunder The Influence - Windward Rush | 11:07 |
| 34. | CerealSnax | 263 | Windward - Spirtual sequel to Pirates! - Ep1? - "Sojourn" (Windward Gameplay) | 20:11 |
| 35. | Zearon | 222 | Windward Killing Time Stream and Pirates | 1:09:55 |
| 36. | The Ceiling Fan Hub | 206 | Hampton Bay Windward II Ceiling Fan (5 of 10) | 1:31 |
| 37. | Notorious Rollers | 158 | Windward Episode 16 : Diplomacy Max | 17:42 |
| 38. | Mortus | 144 | First Look: Windward | 47:45 |
| 39. | Las Scottas | 127 | Windward Let's Play 5 - Buying a New Ship | 13:22 |
| 40. | KilroyWasHere | 111 | Sci-Fi Fantasy Saturday - Windward (PlayMonster) | 23:09 |
| 41. | Shock & Awe Gaming | 94 | Temtem - Blind Playthrough | Day 3 | Windward Fort & First Dojo! | 5:00:06 |
| 42. | TLG | 94 | We Played Windward (Game of the Month Dec 2017) | 29:43 |
| 43. | axiskae | 80 | Windward - 2 Player Co-op - Part 3 - With EvilGok | 50:52 |
| 44. | rvlast | 73 | INFERNO~~~~ | Windward Part 2 | 10:15 |
| 45. | Aun Collective | 61 | Episode #15 - Windward [PC] First Impressions Review | 21:45 |
| 46. | Superbanana Gaming | 44 | Don’t be defeated by the windward!(trails of cold steel music mix) | 1:38 |
| 47. | Jeff | 43 | Gloomhaven Playthrough - Mission 12 - Windward ho | 1:39:34 |
| 48. | MemoryLeakDeath | 40 | Side Quests: Windward | 30:36 |
| 49. | Rampancy | 37 | Let's Play Windward | 22:21 |
| 50. | Just Magikarp | 30 | The Windward Fort - Temtem (co-op) Ep. 4 | 1:14:54 |
| 51. | MrBagelz | 30 | Test Run - Windward! | 1:20:19 |
| 52. | Brascus | 29 | Adventure On The High Seas! | Windward | 21:34 |
| 53. | Insert Coin Theater | 28 | Stream | Let's Try... Windward w/ Jenks, Nathan and Furball! | 2:58:16 |
| 54. | Travel Hotel Reviews | 23 | Hyatt Place Atlanta / Alpharetta / Windward Parkway Review - Alpharetta , United States of America | 1:51 |
| 55. | KittyTeam | 20 | Windward GamePre | 13:55 |
| 56. | Captain Mog | 20 | W is for WINDWARD [GAMES FROM A TO Z] | 28:09 |
| 57. | Kickslc | 17 | Windward ep 3 | 18:17 |
| 58. | EchoingSong | 13 | Temtem Co-op | Windward Fort | Part 15 | 18:16 |
| 59. | Aylad Plays / Gaming and Ambience | 12 | Indie Speed Dating: Windward | 23:03 |
| 60. | Extermideath | 10 | Testing the Stream Function on youtube while playing the game Windward | 15:47 |
| 61. | Vidavis Prime | 9 | LNS: TIME FOR SOME BOATING! Windward Gameplay! | 5:26:07 |
| 62. | MapFlagged | 8 | FL | Buy house at 10158 WINDWARD WAY, Jacksonville, USA | MapFlagged | 3:21 |
| 63. | Sergeant Pepper | 8 | Let's be pirates | First Impressions Windward | Episode 1 | 39:58 |
| 64. | Island Ranger | 8 | Web cam Wednesdays: Windward | 15:00 |
| 65. | High Koala Tea Productions | 6 | The Adventures of Kaptin Kap! - Windward | 25:36 |
| 66. | Artyom Havok | 5 | One-Hour Stream #916 Windward [PC-Steam][2015] | 0:00 |
| 67. | Whatshisface7 | 4 | I'M A CAPTAIN! | Windward part 1 | 22:50 |
| 68. | The Bass is Loaded | 3 | Let's Play Windward Episode 02 - Jerk in a Boat | 16:07 |
| 69. | Dswank | 2 | Windward | 20:45 |
| 70. | Eizen D. Broniac Streams | 2 | Gladius: Climbing up the Windward Steppes | 4:12:41 |
