The work of adhesion between a polydimethylsiloxane (PDMS) elastomer film and a flat diamond tip was measured by instrumented indentation. The results showed that the apparent work of adhesion between the tip and the PDMS film increases with increasing dwell time and retreating velocity; on the other hand, the indentation depth has no significant effect on adhesion. The indentation experiment was analysed with viscoelastic finite element simulations with rate-dependent cohesive elements, from which the time evolution of adhesion was quantitatively implemented into a rate-dependent cohesive-zone law.