| 1. |  Worth A Buy | Windward Review - Worth a Buy? | 167 | Review |
| 2. |  VintageBeef | Let's Play Windward - EP01 - The High Seas | 132 | Let's Play |
| 3. | GuudeBoulderfist | Team Nancy Drew - Windward - Sailing into the Sunset | 108 | |
| 4. |  Noxxis Gaming | How To Play Windtrace 3.3 Rerun Day 1 Event Guide | Windward Arts & Hiding Spots | Genshin Impact | 95 | |
| 5. | muyskerm | PIRATES!? Probably Anyway | Windward Ep. 1 | 92 | |
| 6. | muyskerm | More Quests, More Booty! | Windward Ep. 2 | 90 | |
| 7. | PauseUnpause | Team Nancy Drew plays Windward - Part 4 | 87 | Let's Play |
| 8. | Blitz | Windward - Ep. 1 - The Valiant! - Let's Play | 84 | Let's Play |
| 9. | Tank Fish's Garbage Dump | Roblox Windward Tutorial | 73 | |
| 10. | Quackalope | Windward - Kickstarter Prototype - (Quackalope Review) | 62 | Review |
| 11. | muyskerm | The Region is Ours! | Windward Ep. 5 Feat Jack, Mark, and Yami | 61 | |
| 12. | muyskerm | Teamwork!!!....? | Windward Ep. 4 Feat Jack, Mark, and Yami | 57 | |
| 13. | VintageBeef | Let's Play Windward - EP03 - Southbound! | 52 | Let's Play |
| 14. | VintageBeef | Let's Play Windward - EP02 - Pirates! | 50 | Let's Play |
| 15. | Blitz | Windward - Ep. 2 - Raise the Blue Sails! - Let's Play | 47 | Let's Play |
| 16. | The Dice Tower | Windward Review - with Blake | 46 | Review |
| 17. | Getting Games | Windward Tutorial & Playthrough - JonGetsGames | 41 | Let's Play |
| 18. | rizzler | Underground : Windward - Naval Combat/Exploration Sandbox RPG Gameplay | 40 | |
| 19. | GuudeBoulderfist | Team Nancy Drew - Windward - Setting Sails | 39 | |
| 20. | Pravus | Steamed! | Windward | 36 | |
| 21. | PauseUnpause | Team Nancy Drew plays Windward - Part 1 | 35 | Let's Play |
| 22. | Getting Games | Windward Extended Playthrough - JonGetsGames | 33 | Let's Play |
| 23. | Yippee Ki Yay Mr Falcon | Falcon 1 Shot - Let's Play Windward - Yarr Pirates! - Gameplay Impressions | 30 | Let's Play |
| 24. | Mal | WINDWARD | Let's Try | PC Gameplay | CO-OP w/ IDED | Part 1 | 28 | |
| 25. | GuudeBoulderfist | Team Nancy Drew - Windward - Coming for You Blue | 26 | |
| 26. |  Brodaty | WindWard / Steam / Gameplay | 26 | |
| 27. | muyskerm | Windward, Now With More PhlyDaily! | Windward Ep. 6 | 26 | |
| 28. | muyskerm | Too Many Pirates! | Windward Ep. 7 | 24 | |
| 29. | GuudeBoulderfist | Team Nancy Drew - Windward - Fast Travel | 24 | |
| 30. | PauseUnpause | Team Nancy Drew plays Windward - Part 2 | 24 | Let's Play |
| 31. |  TheWall225 | Winward Gameplay HD ITA #00 - Scopriamolo Insieme | 24 | |
| 32. | Quackalope | Windward - (Quackalope Gameplay) | 23 | |
| 33. | Blitz | Windward - Ep. 7 - Thunder Rolls! - Let's Play | 21 | Let's Play |
| 34. | Blitz | Windward - Ep. 3 - The Deadly Reef! - Let's Play | 21 | Let's Play |
| 35. | Blitz | Windward - Ep. 11 - Testing Online Waters! - Let's Play | 20 | Let's Play |
| 36. | Blitz | Windward - Ep. 13 - More Server Play! - Let's Play | 20 | Let's Play |
| 37. | GloryHoundd | Windward playthrough! | 20 | Let's Play |
| 38. | TheWall225 | Windward Gameplay HD ITA #1 - Tutti a Commerciare | 19 | |
| 39. | Pecktec Games | Windward Review : Notorious Gas Pirates | 19 | Review |
| 40. | ObsidianAnt | Windward - Elite on the High Seas! Trading, Exploring & Combat Gameplay | 19 | |
| 41. | PauseUnpause | Team Nancy Drew plays Windward - Part 3 | 18 | Let's Play |
| 42. | tom.io | Casual Friday: Windward - Early Access [ Gameplay / Deutsch / German ] | 18 | |
| 43. | FailRace | FailRace Play Windward (60FPS) | 17 | |
| 44. | Blitz | Windward - Ep. 6 - The Stealth Mission! - Let's Play | 17 | Let's Play |
| 45. | WhamyKaBlamy | Checking out Windward (Or is that WindwARR'd? Hehehe...) | 17 | |
| 46. | Cinghiali sul Tubo | Windward ita - Uno sguardo approfondito | 17 | |
| 47. | Blitz | Windward - Ep. 15 - The Final Battle - Let's Play | 16 | Let's Play |
| 48. | Blitz | Windward - Ep. 8 - Gaining A Foothold! - Let's Play | 16 | Let's Play |
| 49. |  DrProof | #TeamKrone | Windward - Handliches Pirates für Zwischendurch [Deutsch|German] Gameplay | 16 | Let's Play |
| 50. | Unfiltered Gamer | Windward - Board Game Review | 15 | Review |
| 51. | AvatarXGames | Naval Action #001 ✰ Ahoi Käpten - Willkommen in der Karibik ✰ Gameplay german | 14 | |
| 52. | Blitz | Windward - Ep. 5 - Circling Like Sharks! - Let's Play | 14 | Let's Play |
| 53. | Blitz | Windward - Ep. 12 - Rocking an Instance! - Let's Play | 14 | Let's Play |
| 54. | Naherholungszentrum | Lohnt sich Windward? | Gameplay | Test/Review | Deutsch/German | 14 | Review |
| 55. | MMOs.com | Windward Gameplay - Altay Plays | 14 | Review |
| 56. | GamerZakh | 3 Part Let's Play ► Windward P1 | 13 | Let's Play |
| 57. | Blitz | Windward - Ep. 9 - Farming Some Quests! - Let's Play | 13 | Let's Play |
| 58. | Gamers Nexus | Windward Seafaring Gameplay & Review - Editor's Choice | 13 | Review |
| 59. | Off The Shelf Board Game Reviews | Windward - How to Play | 12 | Guide |
| 60. | Sooo Mungry | Windward Gameplay - High Seas Pirate Battles Arrrr! - Live Stream Highlights (PC, Steam) | 12 | |
| 61. | Button Pushin' Cushion | It's Cool To Suck! | Windward: Eye Of The Storm | 12 | |
| 62. | DocRattie | Windward - #1 Auf den Weiten der Meere | 11 | |
| 63. |  CAPITAIN DOG | WINDWARD GAMEPLAY PT BR | 11 | |
| 64. |  towns nath | Windward FR - Let's play 01 - Ho! Ho! Ho! Matelot! | 10 | Let's Play |
| 65. | Wolfenout Gaming | Windward| Part 7| Show No Quarter Lads!!!!!! | 10 | Show |
| 66. | PlayMV | MisterMV - Indéfinitivement (12/05/2015) | 10 | |
| 67. | Blitz | Windward - Ep. 14 - Ship of the Line! - Let's Play | 10 | Let's Play |
| 68. | Blitz | Windward - Ep. 10 - Poison Fog! - Let's Play | 10 | Let's Play |
| 69. | MonkeyBusinessGaming | Windward: THE END OF WINDWARD - We've Sailed our Course | 10 | |
| 70. | AreYouGaming | Flog Plays and Reviews: Windward | 9 | Review |
| 71. | Tasty Loot Gaming | We Played Windward (Game of the Month Dec 2017) | 9 | |
| 72. | MMOHuts | Windward - PAX East 2015 Dev Interview | 9 | |
| 73. | W92Baj - Minecraft and games | Team Nancy Drew play Windward - 1 | 9 | |
| 74. | DieselDesigns Gaming | Let's Play Windward: EP07: Pirate Captain Boss! WAR Part 2 (Early Access Let's Play 60FPS) | 9 | Let's Play |
| 75. | HAKIMODO | T09 == WINDWARD == Z wiatrem w żaglach - miła gra handlowo-zręcznościowa | 9 | |
| 76. | DieselDesigns Gaming | Let's Play Windward: EP13: #WarWeek Death Follow Us All! Part 3 (Let's Play 60FPS) | 9 | Let's Play |
| 77. | Tantrum House | Windward Board Game Preview | 8 | Preview |
| 78. | Board Game Hero | LET'S PLAY: Windward - Solo Adventure | 8 | |
| 79. | Андроид Андройдыч | Windward - Становимся пиратом и участвуем в морских сражениях на Android | 8 | |
| 80. | Commissar BRO | Windward Gameplay and Impressions | 8 | |
| 81. | Jacky753 | Let's Play Windward Episode One (1080p 60FPS) | 8 | Let's Play |
| 82. | DieselDesigns Gaming | Let's Play Windward: EP06: Royal Brigantine & Pirate WAR! Part.1 (Early Access Let's Play 60FPS) | 8 | Let's Play |
| 83. | LPIndie - Astronomie und Wissenschaft | Let's Play Windward "Chaoscaptain" german | deutsch | 8 | |
| 84. |  Lochtness Gaming | Dagekkie plays Windward! – Episode 01 – A Faction Full of Monsters! | 7 | Let's Play |
| 85. | OneLastMidnight | WINDWARD - PART 1 - STARTING OUT - Let's Play / Gameplay | 7 | Let's Play |
| 86. |  MrAntiFun | Windward V1.00 Trainer +2 | 7 | |
| 87. | MonkeyBusinessGaming | Windward: Upgrading our ships! | 7 | |
| 88. |  Deq | Windward - Android Gameplay | 7 | |
| 89. | MonkeyBusinessGaming | Windward: Sailing to New Lands! | 7 | |
| 90. |  MMO GAMES WORLD | Windward - ОБЗОР морской MMO | 7 | |
| 91. | Tantrum House | Windward Playthru | 7 | |
| 92. |  Northgate | Let's Play/Test Windward #001 (Deutsch/German) - Setzt die Segel Männer! | 7 | Let's Play |
| 93. | Blitz | Windward - Ep. 4 - Tactical Retreat! - Let's Play | 7 | Let's Play |
| 94. | TydyshTVLive | Лизнём Windward Ep1 - Флибустьеры с "Курвы" (Indie Early Access Rec) | 6 | |
| 95. | Off The Shelf Board Game Reviews | Windward - Full Gameplay | 6 | |
| 96. | Off The Shelf Board Game Reviews | Windward - Review | 6 | Review |
| 97. | DieselDesigns Gaming | Let's Play Windward: EP08: Making Gold! (Early Access Let's Play 60FPS) | 6 | Let's Play |
| 98. | Mal | WINDWARD | Let's Try | PC Gameplay | CO-OP w/ IDED | Part 5 | 6 | |
| 99. |  TGN en Español | Underground : Windward - RPG + Acción + Aventura ¿Qué más podemos pedir? | 6 | |
| 100. |  Стримы Игроглаза 🔴 | Windward РЕЙД: ПИРАТЫ И ДРАКОН @ морская MMORPG | 6 | |
