| 1. | steamfrance | Tradewinds Legends Trailer | 10,305 | Preview |
| 2. |  Big Fish Games | Tradewinds Odyssey | 10,129 | |
| 3. | CEO100able | WildTangent Tradewinds (Trial Version) Walkthrough | 5,793 | |
| 4. | steamfrance | Tradewinds Classic Trailer | 3,644 | Preview |
| 5. | Isaac Spencer | Tradewinds Legends Any% Glitchless 1h11m06s | 2,569 | |
| 6. | The Battle Family | Trains at Tradewinds Park in Coconut Creek Florida | 1,316 | |
| 7. | steamfrance | Tradewinds Caravans Trailer | 1,302 | Preview |
| 8. |  Wallace | Tradewinds Classic - OST - Main Menu Theme | 1,040 | |
| 9. | The Battle Family | Horse Back Riding Playground and Bouncy House at Tradewinds Park | 958 | |
| 10. | Hamr102 | Tradewinds Classic Ep.1:Later | 655 | |
| 11. | montgomeryGilmoreBR | Tradewinds | 617 | |
| 12. | Wallace | Tradewinds Classic - OST - Jia-Ching Theme | 506 | |
| 13. | steamfrance | Tradewinds Odyssey Trailer | 444 | Preview |
| 14. | Wallace | Tradewinds Classic - OST - Tanchon Theme | 371 | |
| 15. | Wallace | Tradewinds Classic - OST - Lama Sut Theme | 340 | |
| 16. | Wallace | Tradewinds Classic - OST - Shangri La Theme | 325 | |
| 17. | CheeseCakeCactus | NEW Pirate Ship Trading Game like TRADEWINDS! [ Cactus plays High Seas, High Profits! ] | 318 | |
| 18. | Requisitos Jogos | Tradewinds Caravans - Trailer | 313 | Preview |
| 19. | Adventure Mode TNT | Tradewinds more ADVENTURE | 300 | |
| 20. | Wallace | Tradewinds Classic - OST - Sailing Theme | 292 | |
| 21. | KhaosSN | Khaos Plays DigiPen Games! - Ep. 1 - Tradewind | 283 | |
| 22. | Wallace | Tradewinds Classic - OST - Edamame Theme | 242 | |
| 23. | Isaac Spencer | Tradewinds Legends any% 1h53m34s44ms | 228 | |
| 24. | Wallace | Tradewinds Classic - OST - Combat/Battle Theme | 223 | |
| 25. |  MHA Gaming Channel | Let's Play: Tradewinds Legends (Part 1) - THE ADVENTURE BEGINS... | 163 | |
| 26. | Hamr102 | Tradewinds Classic: Reboot Episode 1 | 140 | |
| 27. | Requisitos Jogos | Tradewinds Classic - Trailer | 116 | Preview |
| 28. | Requisitos Jogos | Tradewinds Legends - Trailer | 105 | Preview |
| 29. | thatcableguy1 | Tradewinds Tai-Pan - 1:30:41 | 88 | |
| 30. | Requisitos Jogos | Tradewinds Odyssey - Trailer | 76 | Preview |
| 31. |  Paoletto 97 | LEGO Gli Incredibili - Sfida "Pesce Grosso!" completata e Tradewind sbloccato | 67 | |
| 32. | Willu | PAC Tradewind WIN 04.08.2011 | 57 | |
| 33. | thatcableguy1 | Tradewinds Expert Trader - 2:44.30 | 49 | |
| 34. | Ronald LeBlanc (EMDream) | Tradewinds Legends: Captain Nandi Patel Full Playthrough | 46 | Let's Play |
| 35. | Ronald LeBlanc (EMDream) | Tradewinds Legends: Captain Hasan Full Playthrough | 29 | Let's Play |
| 36. | thatcableguy1 | Tradewinds Tai-Pan - 26:11.16 | 22 | |
| 37. | TowMeToTheMoon | Tradewinds RPG - Hopping the Ferry (ASA) | 16 | |
| 38. | Thetoon2013 | Lets play some Tradewinds legends | 14 | Let's Play |
| 39. |  Yahbob | ATLAS - Riding the Tradewinds and Taking down Ghosties - Supremegaming Server | 14 | |
| 40. | Ronald LeBlanc (EMDream) | Tradewinds: Classic Merchant Captain Douglas McGowan Full Playthrough | 13 | |
| 41. | MapFlagged | NZ | Buy house at 4 Tradewinds Drive, Whitby, Porirua, Wellington, NewZealand | MapFlagged | 11 | |
| 42. | Thetoon2013 | Lets Play some Tradewinds Legends | 10 | Let's Play |
| 43. | Ronald LeBlanc (EMDream) | Tradewinds: Classic Pirate Captain Gossamer Full Playthrough | 10 | |
| 44. |  Ireland Deity | Magic The Gathering MTG Kaladesh Aether Tradewinds 28.03.17 | 9 | |
| 45. | Ronald LeBlanc (EMDream) | Tradewinds: Classic Pirate Captain Petra Gale Full Playthrough | 8 | Let's Play |
| 46. | Ronald LeBlanc (EMDream) | Tradewinds Legends: Captain Tiger Bai Full Playthrough | 8 | Let's Play |
| 47. | Ronald LeBlanc (EMDream) | Tradewinds Legends: Captain Rihana Sayar Full Playthrough | 7 | Let's Play |
| 48. |  petsasjim1 | Tradewinds Legends HYPERSPIN IBM PC MICROSOFT WINDOWS NOT MINE VIDEOS | 5 | |
| 49. | Ronald LeBlanc (EMDream) | Tradewinds: Classic Merchant Captain Madame Tso Full Playthrough | 3 | |
| 50. | TowMeToTheMoon | Tradewinds RP - Moon - 4/12 | 3 | |
| 51. | Thetoon2013 | Lets Play some Tradewinds Legends | 1 | Let's Play |
