there are two ways to compare the two

1. As Peers
if this is the case then hands down the ipod or any cheap modern digital music player can win over it in terms of versatility, longevity, robustness, sound consisteny, and possibly quality.

2 As Trail Blazers
In many respects they are on equal footing ie miniaturisation, using latest tech, wow factor.

But one thing the ipod just cant beat the walkman at is it did it first. Imho it was a greater leap from records to mini tape than from tape to hard disk for th hard disks and memory are and were more common when the ipod came out as opposed to the miniturisation of the tapes