| 1. |  Worth A Buy | Windward Review - Worth a Buy? | 85,198 | Review |
| 2. | FailRace | FailRace Play Windward (60FPS) | 4,881 | |
| 3. | ObsidianAnt | Windward - Elite on the High Seas! Trading, Exploring & Combat Gameplay | 4,730 | |
| 4. | MonkeyBusinessGaming | Windward: Upgrading our ships! | 3,006 | |
| 5. | GamerZakh | 3 Part Let's Play ► Windward P1 | 2,722 | Let's Play |
| 6. | 1738 Creations | Raspberry Pi 4 - Windward Dedicated Server Setup and Performance | 1,670 | Guide |
| 7. | W92Baj - Minecraft and games | Team Nancy Drew play Windward - 1 | 851 | |
| 8. | MonkeyBusinessGaming | Windward: Smuggling, Questing and Trading, Monkey Business style! - Part One | 801 | |
| 9. | GamerZakh | 3 Part Let's Play ► Windward P2 | 782 | Let's Play |
| 10. | GamerZakh | 3 Part Let's Play ► Windward P3 | 754 | Let's Play |
| 11. | W92Baj - Minecraft and games | Team Nancy Drew play Windward - 2 | 706 | |
| 12. | MonkeyBusinessGaming | Windward: Smuggling, Questing and Trading, Monkey Business style! - Part Two | 594 | |
| 13. | ConflictNerd | ConflictNerd Plays... - Windward | 589 | Let's Play |
| 14. | Dandelion-Utilitarian | Windward - A Linux Game | 577 | |
| 15. | C&NOnline | Windward Review | 508 | Review |
| 16. | MonkeyBusinessGaming | Windward: THE END OF WINDWARD - We've Sailed our Course | 444 | |
| 17. | MonkeyBusinessGaming | Windward: Sailing to New Lands! | 435 | |
| 18. | MonkeyBusinessGaming | Windward: We've Made a Mistake.... | 386 | |
| 19. | Button Pushin' Cushion | It's Cool To Suck! | Windward: Eye Of The Storm | 74 | |
| 20. | Northstorm Gaming | Windward - Beginners Journey - Let's Play S1E01 | 50 | Let's Play |
| 21. | CptAylott | Little Look At: Windward -The sea life- | 47 | |
| 22. | Crownos | Windward - Sailing The High Seas, What Should We Be? Pirate? Trader? or Something Inbetween? | 32 | |
| 23. | Northstorm Gaming | Windward - New Schooner Ship - Let's Play S1E03 | 22 | Let's Play |
| 24. | VarietyDefenceForce | VGUK - Yreon Plays Windward - Ghost Lake | 16 | Let's Play |
| 25. | vertual pix | Windward #1 (Pass me Grog) | 11 | |
| 26. | Trophy Time | I Forced My Friends To Play Windward | 10 | |
| 27. | Silens-Venatus | Chapter 4: Windward Fort - Belsoto Encounter! [TEMTEM] | 8 | |
| 28. | VarietyDefenceForce | VGUK - EmmaSurrender Plays Windward - Ghost Lake | 7 | Let's Play |
| 29. | VarietyDefenceForce | VGUK - Yreon Plays Windward | 5 | Let's Play |
| 30. | VarietyDefenceForce | VGUK - Yreon Plays Windward - The Ring / The Short Straw | 3 | Let's Play |
| 31. | Odin Fury | On Air With Odin Playing Windward! Adventure Waits For No Release Date! | 1 | |
