| 1. |  Blitz | 470,782 | Windward - Ep. 15 - The Final Battle - Let's Play | 32:34 |
| 2. |  VintageBeef | 114,418 | Let's Play Windward - EP03 - Southbound! | 21:09 |
| 3. | PauseUnpause | 53,920 | Team Nancy Drew plays Windward - Part 4 | 21:28 |
| 4. | Getting Games | 35,609 | Windward Extended Playthrough - JonGetsGames | 48:00 |
| 5. |  DrProof | 22,931 | Windward - Handliches Pirates für Zwischendurch [Deutsch|German] Gameplay | 36:02 |
| 6. | DieselDesigns Gaming | 16,689 | Let's Play Windward: EP22: Finale with a FaceCam! (60FPS) | 47:58 |
| 7. | Welsknight Gaming | 15,361 | Let's Play Windward - Ep. 5: The Last Stand | Windward Gameplay/Walkthrough | 24:12 |
| 8. | Dad's Gaming Addiction | 10,844 | DGA Live-streams: Windward (Ep. 14 - Gameplay / Let's Play) | 1:01:58 |
| 9. | One Last Midnight | 7,084 | Windward Gameplay - TWO POINTS PORT CAPTAIN! - Part 15 - Lets Play Windward | 1:06:03 |
| 10. |  GamerZakh | 4,258 | 3 Part Let's Play ► Windward P3 | 26:09 |
| 11. |  towns nath | 4,197 | Windward FR - Let's play 02 - Le PvE ça donne quoi? | 9:34 |
| 12. |  Northgate | 2,465 | Let's Play/Test Windward #001 (Deutsch/German) - Setzt die Segel Männer! | 20:44 |
| 13. | MakiMaki | 2,383 | Windward #50 - Verbissen bis zum Schluss - Let's Play [german/gameplay] | 31:05 |
| 14. | Yippee Ki Yay Mr Falcon | 2,164 | Falcon 1 Shot - Let's Play Windward - Yarr Pirates! - Gameplay Impressions | 14:19 |
| 15. |  Lochtness Gaming | 1,864 | Dagekkie plays Windward! – Episode 07 – Tough Pirates | 16:51 |
| 16. | TimmexTV | 1,260 | Windward 34 Ganze Insel Beschlagnahmt - [ Deutsch | German | Gameplay | Let's Play ] | 20:42 |
| 17. | GloryHoundd | 1,238 | Windward playthrough! | 1:25:11 |
| 18. | It's Jackson | 1,037 | Windward Let's Play EP08 | BATTLING OTHER PLAYERS! | 17:37 |
| 19. | ConflictNerd | 589 | ConflictNerd Plays... - Windward | 1:26:19 |
| 20. |  Kokoplays MB | 450 | Kokoplays Windward - Ep. 13 - Koko's Tortuga | 21:17 |
| 21. | Bay 01 | 391 | Let's Play: Windward - Hoisting sails with Cap'n Robobeard (Part 8) | 14:21 |
| 22. | The Pixel Pirate | 265 | Irresistible Indie - Windward | 16:01 |
| 23. | Brilliant Chicken | 226 | Windward Gameplay - Let's Play Stream #1 | 2:43:48 |
| 24. | Faize Plays | 185 | Faize Plays: Windward 0 -100 - Part 2 - Seige Towers hurt | 40:22 |
| 25. |  Shitty Wizard | 176 | Shitty Wizard plays WindWard (extra virgin profanity!) | 8:43 |
| 26. | Jacky753 | 137 | Let's Play Windward Episode One (1080p 60FPS) | 12:37 |
| 27. | Las Scottas | 127 | Windward Let's Play 5 - Buying a New Ship | 13:22 |
| 28. | Drago Basler | 103 | Let's Play Windward Part 2: Map 2 und 3 erkunden! (deutsch) (interaktiv) (Full HD) | 26:34 |
| 29. | Shock & Awe Gaming | 94 | Temtem - Blind Playthrough | Day 3 | Windward Fort & First Dojo! | 5:00:06 |
| 30. | ALP | 93 | WINDWARD - "Schiffe versenken" - reingeschaut #2 | 28:28 |
| 31. | Northstorm Gaming | 72 | Windward - New Schooner Ship - Let's Play S1E03 | 25:20 |
| 32. | Patrick Finie | 71 | Mir Plays on Linux Windward RAID night Live Pt i dont remember what numbers are ! | 3:36:31 |
| 33. | Die OpaRazzi Tutorials | 66 | Let`s Play Tutorial von Windward - deutsch | 35:20 |
| 34. | VampireLogan | 54 | VL Variety Gaming - Let's Play Windward | 1:10:40 |
| 35. | Rampancy | 37 | Let's Play Windward | 22:21 |
| 36. | VarietyDefenceForce | 31 | VGUK - Yreon Plays Windward | 24:11 |
| 37. | JacePl | 24 | Handeln und Kapern | Lets Play | Windward #09 | | 30:18 |
| 38. | Travel Hotel Reviews | 23 | Hyatt Place Atlanta / Alpharetta / Windward Parkway Review - Alpharetta , United States of America | 1:51 |
| 39. | kmdbaby | 3 | Gladius Playthrough Part 59 - Windward Steppes: Onohaar | 30:41 |
| 40. | The Bass is Loaded | 2 | Let's Play Windward Episode 02 - Jerk in a Boat | 16:07 |
