| 1. |  Worth A Buy | Windward Review - Worth a Buy? | 167 | Review |
| 2. | ObsidianAnt | Windward - Elite on the High Seas! Trading, Exploring & Combat Gameplay | 19 | |
| 3. | FailRace | FailRace Play Windward (60FPS) | 17 | |
| 4. | GamerZakh | 3 Part Let's Play ► Windward P1 | 13 | Let's Play |
| 5. | Button Pushin' Cushion | It's Cool To Suck! | Windward: Eye Of The Storm | 12 | |
| 6. | MonkeyBusinessGaming | Windward: THE END OF WINDWARD - We've Sailed our Course | 10 | |
| 7. | W92Baj - Minecraft and games | Team Nancy Drew play Windward - 1 | 9 | |
| 8. | MonkeyBusinessGaming | Windward: Upgrading our ships! | 7 | |
| 9. | MonkeyBusinessGaming | Windward: Sailing to New Lands! | 7 | |
| 10. | W92Baj - Minecraft and games | Team Nancy Drew play Windward - 2 | 6 | |
| 11. | MonkeyBusinessGaming | Windward: Smuggling, Questing and Trading, Monkey Business style! - Part One | 5 | |
| 12. | 1738 Creations | Raspberry Pi 4 - Windward Dedicated Server Setup and Performance | 5 | Guide |
| 13. | Dandelion-Utilitarian | Windward - A Linux Game | 5 | |
| 14. | GamerZakh | 3 Part Let's Play ► Windward P3 | 4 | Let's Play |
| 15. | GamerZakh | 3 Part Let's Play ► Windward P2 | 3 | Let's Play |
| 16. | MonkeyBusinessGaming | Windward: Smuggling, Questing and Trading, Monkey Business style! - Part Two | 3 | |
| 17. | Northstorm Gaming | Windward - Beginners Journey - Let's Play S1E01 | 2 | Let's Play |
| 18. | Northstorm Gaming | Windward - New Schooner Ship - Let's Play S1E03 | 2 | Let's Play |
| 19. | Crownos | Windward - Sailing The High Seas, What Should We Be? Pirate? Trader? or Something Inbetween? | 1 | |
