| 1. Round | 18/09/2008 | Borac Čačak | - | AFC Ajax | 1:4 | ||||
| 1. Round | 02/10/2008 | AFC Ajax | - | Borac Čačak | 2:0 | ||||
| Group F | 23/10/2008 | Aston Villa | - | AFC Ajax | 2:1 |  |
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| Group F | 06/11/2008 | AFC Ajax | - | MŠK Žilina | 1:0 | ||||
| Group F | 27/11/2008 | Hamburger SV | - | AFC Ajax | 0:1 | ||||
| Group F | 17/12/2008 | AFC Ajax | - | Slavia Praha | 2:2 | ||||
| 3. Round | 19/02/2009 | ACF Fiorentina | - | AFC Ajax | 0:1 |  |
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| 3. Round | 26/02/2009 | AFC Ajax | - | ACF Fiorentina | 1:1 | ||||
| Round of 16 | 12/03/2009 | Olympique Marseille | - | AFC Ajax | 2:1 | |
Belgium
