| 1. |  GomesDaLegend | I Spent $1 On This Retro PS1 MLB The Show Game... MLB 99 Gameplay | 43 | Show |
| 2. | igcompany | MLB 99 PS1 Gameplay HD | 15 | |
| 3. | VideoGaming4U | MLB 99 (PlayStation) - New York Yankees vs. New York Mets | 13 | Let's Play |
| 4. | Charm City Gamer | Orioles VS White Sox - MLB 99 | 12 | |
| 5. | ChaoEmperor Productions LLC | MLB 99 Sony PlayStation Gameplay Sample (PS1) | 12 | Let's Play |
| 6. | Charm City Gamer | MLB 99 Intro | 9 | |
| 7. | astrodome1994 | MLB 99 (PS1) Menu Theme | 7 | |
| 8. | 10min Gameplay | MLB 99 ... (PS1) Gameplay | 6 | Let's Play |
| 9. | Steve Klebrowski | MLB 99 PlayStation gameplay | 5 | |
| 10. | Old School Gaming | Playstation Longplay - MLB 99 | 5 | Let's Play |
| 11. | The Sports Show | MLB 99 PS1 Gameplay | 4 | |
| 12. |  aroo of fighters | Official US Playstation Magazine - Demo Disc 8 | 4 | |
| 13. | Game Saloon | All MLB PS1 Intros Vol. 1 | 4 | |
| 14. | ClassicGameGems | Classic Game Gems: MLB 99 Preview Movie | 3 | Preview |
| 15. | PS1 OST | MLB 99 (USA) OST | 3 | |
| 16. | 30-30 Club - Baseball Video Game Encyclopedia | MLB 99 (PS1) - Gameplay | 2 | |
| 17. | Bulletfreak224 Gaming | MLB 99(PlayStation)Gameplay | 2 | Let's Play |
| 18. | GamePlayStation | MLB 99 -- Gameplay (PS1) | 2 | |
| 19. | someother1ne | MLB 99 Baseball PS1/ PSX Widescreen @ 60fps PCSXR-PGXP (Sony, 1998) | 1 | |
| 20. |  Old Dusty Games | MLB 99 [Psx] - Trailer 2 | 1 | |
| 21. | PS1 OST | MLB 99 (USA) - All FMVs | 1 | |
| 22. | Old Dusty Games | MLB '99 [Psx] - Intro | 1 | |
| 23. | Michael Soehnlen | MLB 99 PS1; Cleveland Indians VS. Houston Astros | 1 | |
| 24. | Pichu London Sports | MLB 99 | Sports Game Ballparks 🏟 ⚾️ | 1 | Let's Play |
| 25. | CraftySymbiote | MLB '99 | Official US Playstation Magazine Demo Disc 08 | 1 | |
