| 1. | ApolloIsMyCoPilot | 51,449 | Let's Play! Oregon Trail 2 - Part 3 - Go, Video Game Characters, Go! | 17:56 |
| 2. |  Steven Thomas Gaming | 46,930 | Oregon Trail II: Livestream 05/23 - Episode 20 | 1:14:02 |
| 3. | quill18 | 27,175 | Let's Play: Oregon Trail 2 | 1:34:20 |
| 4. |  BlackShadow993 | 20,434 | Let's Play The Oregon Trail 2 Pt.16: A Race Against Mother Nature | 41:03 |
| 5. | Cybie1111 | 5,349 | Let's Play The Oregon Trail 2: Teacher Run as Trail Guide | Channel Update 4-2017 | 16:23 |
| 6. | DarkValentine1984 | 4,413 | DV Plays: The Oregon Trail 2 - One more time XD | 59:15 |
| 7. | killerassassin | 1,729 | Lets Play Oregon Trail 2 as Senior Citizens 2.0 | 28:46 |
| 8. | TheLeastExpected23 | 1,657 | Let's Play Oregon Trail II Part 3: Tense moments, hunting included! | 14:20 |
| 9. | Slail | 1,289 | Let's Play Oregon Trail II - We Found Another Fort | 1:03:12 |
| 10. | 4Player Archives | 790 | 4Player - Brad plays Oregon Trail [2] | 32:57 |
| 11. | Linda THE GAMER GAL | 355 | Let's Play Oregon Trail II | 54:31 |
| 12. | ballerscuba | 177 | Back in Time - Oregon Trail II Part 5 | 14:22 |
| 13. | Steven Thomas Live | 160 | Oregon Trail 2 - Old School Stream - Episode 4 | 49:28 |
| 14. | RetroNostalgia | 94 | RetroNostalgia Let's Play Oregon Trail II, To Oregon City Maybe | 34:08 |
| 15. | A-to-J Plays | 80 | A-to-J Adventures: The Oregon Trail II (Windows) | Difficulties, Bad Choices, Deadly Winters | 1:31:03 |
| 16. | ShepardKinz | 23 | Webby Plays!: Oregon Trail [2] | 7:04 |
| 17. | Planet Bu | 18 | Oregon Trail 2 Gameplay (1995): DRAGON BALL Z Ed. S5 E1: Can Our Super Saiyan Friends Help Us Win!? | 25:42 |
