| 1. |  JS Productions | 902 | Good vs Evil (Simply Chess) | 9:47 |
| 2. | The WeebGamer | 463 | Chessmaster (Snes) vs Simply Chess | 10:03 |
| 3. | Ayumu Kagami | 343 | Simply Chess - Kagami Review - | 7:59 |
| 4. | MLG Squid | 179 | Minecraft: SIMPLY CHESS! - Marketplace Mini-Game | 50:29 |
| 5. | OhJey | 159 | Simply Chess but NOTHING was Simple | 17:55 |
| 6. | Sir Large Gaming | 143 | Simply Chess - Broken Chess Metagame 2017 no scope XXX burping sound effects | 24:15 |
| 7. | 90 Bears Project | 139 | Simply Chess Watch No Game No Life Instead | 40:43 |
| 8. | KhasAdun | 31 | Let's Try Simply Chess (F2P Chess game) | 16:17 |
| 9. | Aun Collective | 24 | DOS Shareware vs. Steam F2P #01 - Combat Checkers v. SimplyChess | 32:12 |
| 10. | The Double Experience | 20 | Simply Chess - Double-OP | 13:51 |
| 11. | Shook50 | 16 | Two Broke Gamers Simply Chess (Checking All the Mates) | 50:16 |
| 12. | Planetarygamers | 15 | Simply Chess! (The Fall Of The King) | 21:32 |
| 13. | DYMABASE | 11 | 🔴 Simply Chess (PC) Gameplay/Walkthrough DEMO | DQP Gaming Live Stream | 12:40 |
| 14. | S1rRook1eTheGam3r | 11 | Simply Chess: I Have Beginner's Chess Skills | 28:19 |
| 15. | Ryan Medrano | 9 | Simply Chess - Difficulty Level 10 | 5:11 |
| 16. | phalxor | 6 | Simply Chess 9-17-15 | 44:11 |
| 17. | unbudgingsalmon | 6 | My First Chess Game in 3 Years - Simply Chess Ft. My DnD Group | 13:52 |
| 18. | Splazer Productions | 6 | Simply Chess | 12:38 |
| 19. | DerAssi | 4 | DerAssi Simply Chess Virtual Chess Battle #01 | 35:31 |
