| 1. |  VintageBeef | Let's Play Windward - EP01 - The High Seas | 69,439 | Let's Play |
| 2. | rizzler | Underground : Windward - Naval Combat/Exploration Sandbox RPG Gameplay | 49,148 | |
| 3. | VintageBeef | Let's Play Windward - EP02 - Pirates! | 26,512 | Let's Play |
| 4. | PauseUnpause | Team Nancy Drew plays Windward - Part 1 | 22,639 | Let's Play |
| 5. | VintageBeef | Let's Play Windward - EP03 - Southbound! | 18,467 | Let's Play |
| 6. | PauseUnpause | Team Nancy Drew plays Windward - Part 2 | 11,214 | Let's Play |
| 7. | PauseUnpause | Team Nancy Drew plays Windward - Part 3 | 10,076 | Let's Play |
| 8. | PauseUnpause | Team Nancy Drew plays Windward - Part 4 | 9,991 | Let's Play |
| 9. | Yes Guy Gaming | Windward Game Review | 7,826 | Review |
| 10. | Brilliant Chicken | Windward Gameplay - Let's Play Stream #1 | 226 | Let's Play |
| 11. | Loocharagaming | Hunting Pirates And Sailing The Seas! - Windward Multiplayer Server Stream | 150 | |
| 12. | Brilliant Chicken | Windward Bug - Cant Join Anything!!!! | 132 | |
| 13. | SkidRowTrash | Lets Try Games - WINDWARD | 115 | |
| 14. | Christonian | Indie Showcase Windward | 71 | Show |
| 15. | Christonian | Indie Showcase Windward 2 | 54 | Show |
| 16. | VampireLogan | VL Variety Gaming - Let's Play Windward | 54 | Let's Play |
| 17. | PCoutcast | NEWBIE TUESDAY: Windward | 41 | |
| 18. | LaidBack Gaming Network | WindWard [PC/Steam] | 41 | |
| 19. | DFuxa Plays | DFuxa Explores - Windward | 20 | |
| 20. | Sharlenwar | Windward ~ EP 1 ~ Exploring New Territory | 18 | |
| 21. | Sharlenwar | Windward ~ EP 0 ~ First Impressions | 15 | |
| 22. | Sharlenwar | Windward ~ EP 2 ~ Pirates Driven Out | 11 | |
