| 2022-12-27 |  Loocharagaming | Hunting Pirates And Sailing The Seas! - Windward Multiplayer Server Stream | 2:19:05 | 150 |
| 2021-12-31 | VampireLogan | VL Variety Gaming - Let's Play Windward | 1:10:40 | 54 |
| 2017-06-28 | DFuxa Plays | DFuxa Explores - Windward | 56:45 | 20 |
| 2016-03-01 | Yes Guy Gaming | Windward Game Review | 4:23 | 7,826 |
| 2016-01-25 | SkidRowTrash | Lets Try Games - WINDWARD | 32:56 | 115 |
| 2016-01-11 | Brilliant Chicken | Windward Bug - Cant Join Anything!!!! | 2:29 | 132 |
| 2016-01-06 | Brilliant Chicken | Windward Gameplay - Let's Play Stream #1 | 2:43:48 | 226 |
| 2015-11-14 | Christonian | Indie Showcase Windward 2 | 15:52 | 54 |
| 2015-11-10 | Christonian | Indie Showcase Windward | 15:01 | 71 |
| 2015-07-03 | Sharlenwar | Windward ~ EP 2 ~ Pirates Driven Out | 14:51 | 11 |
| 2015-07-01 | Sharlenwar | Windward ~ EP 1 ~ Exploring New Territory | 27:08 | 18 |
| 2015-06-25 | Sharlenwar | Windward ~ EP 0 ~ First Impressions | 30:39 | 15 |
| 2015-05-26 | PCoutcast | NEWBIE TUESDAY: Windward | 24:47 | 41 |
| 2015-04-24 | PauseUnpause | Team Nancy Drew plays Windward - Part 4 | 21:28 | 9,991 |
| 2015-04-22 | LaidBack Gaming Network | WindWard [PC/Steam] | 9:35 | 41 |
| 2015-04-22 | PauseUnpause | Team Nancy Drew plays Windward - Part 3 | 20:38 | 10,076 |
| 2015-04-22 | VintageBeef | Let's Play Windward - EP03 - Southbound! | 21:09 | 18,467 |
| 2015-04-20 | VintageBeef | Let's Play Windward - EP02 - Pirates! | 21:58 | 26,512 |
| 2015-04-20 | PauseUnpause | Team Nancy Drew plays Windward - Part 2 | 21:57 | 11,214 |
| 2015-04-18 | VintageBeef | Let's Play Windward - EP01 - The High Seas | 20:25 | 69,439 |
| 2015-04-18 | PauseUnpause | Team Nancy Drew plays Windward - Part 1 | 20:23 | 22,639 |
| 2014-11-13 | rizzler | Underground : Windward - Naval Combat/Exploration Sandbox RPG Gameplay | 18:20 | 49,148 |
