| 03 May 09 | r27  |  Estoril Open Garcia Lopez vs Gonzalez |
| 04 May 09 | r27 | Estoril Open Gicquel vs Andujar |
| 04 May 09 | r27 | Estoril Open Nalbandian vs Capdeville |
| 04 May 09 | r27 | Estoril Open Simon vs Kendrick |
| 04 May 09 | r27 | Estoril Open Hernandez vs Machado |
| 04 May 09 | r27 | Estoril Open Fish vs Gabashvili |
| 05 May 09 | r27 | Estoril Open Serra vs Junqueira |
| 05 May 09 | r27 | Estoril Open Montanes vs Sweeting |
| 05 May 09 | r27 | Estoril Open Ferrer vs Gimeno Traver |
| 05 May 09 | r27 | Estoril Open Greul vs Hocevar |
| 05 May 09 | r27 | Estoril Open Navarro Pastor vs Martin |
| 05 May 09 | r27 | Estoril Open Davydenko vs Golubev |
| 05 May 09 | r27 | Estoril Open Ferrero vs Kukushkin |
| 05 May 09 | r27 | Estoril Open Monaco vs Cuevas |
| 06 May 09 | r27 | Estoril Open Fognini vs Gaudio |
| 06 May 09 | r27 | Estoril Open Blake vs Gil |
| 06 May 09 | r27 | Estoril Open Gonzalez vs Capdeville |
| 06 May 09 | r27 | Estoril Open Fish vs Navarro Pastor |
| 06 May 09 | r27 | Estoril Open Davydenko vs Ferrero |
| 06 May 09 | r27 | Estoril Open Ferrer vs Hernandez |
| 07 May 09 | r27 | Estoril Open Montanes vs Greul |
| 07 May 09 | r27 | Estoril Open Blake vs Gicquel |
| 07 May 09 | r27 | Estoril Open Monaco vs Serra |
| 07 May 09 | r27 | Estoril Open Simon vs Fognini |
| 08 May 09 | r27 | Estoril Open Hernandez vs Capdeville |
| 08 May 09 | r27 | Estoril Open Davydenko vs Fish |
| 08 May 09 | r27 | Estoril Open Simon vs Montanes |
| 08 May 09 | r27 | Estoril Open Blake vs Serra |
| 09 May 09 | r27 | Estoril Open Montanes vs Capdeville |
| 10 May 09 | r27 | Estoril Open Davydenko vs Blake |
| 10 May 09 | r27 | Estoril Open Blake vs Montanes |
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