| 1. |  Worth A Buy | 85,198 | Windward Review - Worth a Buy? | 8:22 |
| 2. | MonkeyBusinessGaming | 5,666 | Windward: THE END OF WINDWARD - We've Sailed our Course | 2:45 |
| 3. | FailRace | 4,881 | FailRace Play Windward (60FPS) | 22:21 |
| 4. | ObsidianAnt | 4,730 | Windward - Elite on the High Seas! Trading, Exploring & Combat Gameplay | 18:47 |
| 5. | GamerZakh | 4,258 | 3 Part Let's Play ► Windward P3 | 26:09 |
| 6. | 1738 Creations | 1,670 | Raspberry Pi 4 - Windward Dedicated Server Setup and Performance | 13:16 |
| 7. | W92Baj - Minecraft and games | 1,557 | Team Nancy Drew play Windward - 2 | 22:22 |
| 8. | ConflictNerd | 589 | ConflictNerd Plays... - Windward | 1:26:19 |
| 9. | Dandelion-Utilitarian | 577 | Windward - A Linux Game | 14:39 |
| 10. | C&NOnline | 508 | Windward Review | 6:01 |
| 11. | Button Pushin' Cushion | 74 | It's Cool To Suck! | Windward: Eye Of The Storm | 10:57 |
| 12. | Northstorm Gaming | 72 | Windward - New Schooner Ship - Let's Play S1E03 | 25:20 |
| 13. | CptAylott | 47 | Little Look At: Windward -The sea life- | 9:26 |
| 14. | Crownos | 32 | Windward - Sailing The High Seas, What Should We Be? Pirate? Trader? or Something Inbetween? | 3:05:44 |
| 15. | VarietyDefenceForce | 31 | VGUK - Yreon Plays Windward | 24:11 |
| 16. | vertual pix | 11 | Windward #1 (Pass me Grog) | 35:05 |
| 17. | Silens-Venatus | 8 | Chapter 4: Windward Fort - Belsoto Encounter! [TEMTEM] | 1:03:05 |
| 18. | Odin Fury | 1 | On Air With Odin Playing Windward! Adventure Waits For No Release Date! | 1:53:49 |
