Is wireline depth always deeper than the LWD depth?

In most cases, the wireline depth is deeper than the LWD Depth.

The cable stretches more than the pipe stretch of LWD string.

But the good thing is, the cable stretch can be corrected, while the LWD stretch cannot be corrected.

The first wireline run must be run according to the first run in hole / primary depth control procedure. All the subsequent wireline runs will be referred to the first run.
However, there are a few occasions where the wireline depth is shallower than the LWD depth. In this case, you need to relook at the wireline and LWD depths.