| 2024-01-10 |  Crownos | Windward - Sailing The High Seas, What Should We Be? Pirate? Trader? or Something Inbetween? | 3:05:44 | 32 |
| 2023-07-04 | Silens-Venatus | Chapter 4: Windward Fort - Belsoto Encounter! [TEMTEM] | 1:03:05 | 8 |
| 2022-12-22 | Trophy Time | I Forced My Friends To Play Windward | 1:52:05 | 10 |
| 2021-01-18 | Button Pushin' Cushion | It's Cool To Suck! | Windward: Eye Of The Storm | 10:57 | 74 |
| 2019-07-29 | 1738 Creations | Raspberry Pi 4 - Windward Dedicated Server Setup and Performance | 13:16 | 1,670 |
| 2018-05-02 | vertual pix | Windward #1 (Pass me Grog) | 35:05 | 11 |
| 2018-03-12 | Odin Fury | On Air With Odin Playing Windward! Adventure Waits For No Release Date! | 1:53:49 | 1 |
| 2017-08-17 | Dandelion-Utilitarian | Windward - A Linux Game | 14:39 | 577 |
| 2016-02-02 | Northstorm Gaming | Windward - New Schooner Ship - Let's Play S1E03 | 25:20 | 22 |
| 2016-01-28 | Northstorm Gaming | Windward - Beginners Journey - Let's Play S1E01 | 20:10 | 50 |
| 2015-09-18 | ObsidianAnt | Windward - Elite on the High Seas! Trading, Exploring & Combat Gameplay | 18:47 | 4,730 |
| 2015-07-18 | GamerZakh | 3 Part Let's Play ► Windward P3 | 26:09 | 754 |
| 2015-07-15 | GamerZakh | 3 Part Let's Play ► Windward P2 | 28:31 | 782 |
| 2015-07-13 | GamerZakh | 3 Part Let's Play ► Windward P1 | 49:59 | 2,722 |
| 2015-07-01 | MonkeyBusinessGaming | Windward: THE END OF WINDWARD - We've Sailed our Course | 2:45 | 444 |
| 2015-06-24 | MonkeyBusinessGaming | Windward: We've Made a Mistake.... | 4:30 | 386 |
| 2015-06-10 | MonkeyBusinessGaming | Windward: Upgrading our ships! | 9:36 | 3,006 |
| 2015-06-03 | MonkeyBusinessGaming | Windward: Sailing to New Lands! | 11:46 | 435 |
| 2015-06-02 | C&NOnline | Windward Review | 6:01 | 508 |
| 2015-05-29 | MonkeyBusinessGaming | Windward: Smuggling, Questing and Trading, Monkey Business style! - Part Two | 12:22 | 594 |
| 2015-05-25 | MonkeyBusinessGaming | Windward: Smuggling, Questing and Trading, Monkey Business style! - Part One | 15:21 | 801 |
| 2015-05-16 | ConflictNerd | ConflictNerd Plays... - Windward | 1:26:19 | 589 |
| 2015-05-14 | FailRace | FailRace Play Windward (60FPS) | 22:21 | 4,881 |
| 2015-05-05 | Worth A Buy | Windward Review - Worth a Buy? | 8:22 | 85,198 |
| 2015-04-21 | W92Baj - Minecraft and games | Team Nancy Drew play Windward - 2 | 22:22 | 706 |
| 2015-04-20 | W92Baj - Minecraft and games | Team Nancy Drew play Windward - 1 | 21:27 | 851 |
| 2015-01-06 | VarietyDefenceForce | VGUK - Yreon Plays Windward | 24:11 | 5 |
| 2014-10-26 | CptAylott | Little Look At: Windward -The sea life- | 9:26 | 47 |
| 2013-06-18 | VarietyDefenceForce | VGUK - EmmaSurrender Plays Windward - Ghost Lake | 14:19 | 7 |
| 2013-06-17 | VarietyDefenceForce | VGUK - Yreon Plays Windward - The Ring / The Short Straw | 19:31 | 3 |
| 2013-06-12 | VarietyDefenceForce | VGUK - Yreon Plays Windward - Ghost Lake | 20:17 | 16 |
