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Date: 15 August 2008
Summary
Semi-final 1
| Rank | Name | Nation | Time |
| 1 | Michael Phelps | USA | 50.97 |
| 2 | Andrew Lauterstein | AUS | 51.27 |
| 3 | Jason Dunford | KEN | 51.33 |
| 4 | Ryan Pini | PNG | 51.62 |
| 5 | Shi Feng | CHN | 51.68 |
| 6 | Albert Subirats | VEN | 51.82 |
| 7 | Sergii Breus | UKR | 52.05 |
| 8 | Kaio Almeida | BRA | 52.32 |
| Rank | Name | Nation | Time |
| 1 | Milorad Cavic | SRB | 50.92 |
| 2 | Ian Crocker | USA | 51.27 |
| 3 | Andriy Serdinov | UKR | 51.41 |
| 4 | Takuro Fujii | JPN | 51.59 |
| 5 | Peter Mankoc | SLO | 51.80 |
| 6 | Corney Swanepoel | NZL | 52.01 |
| 7 | Lyndon Ferns | RSA | 52.18 |
| 8 | Frederick Bousquet | FRA | 52.94 |