Hi,
It really depends on Your playback rules as MM is buffering at the end of track so if you have overlap enabled and remove silence it is possible that it simply execute repeat track from start.

I tested on My PC and can't replicate.

Hello Devs,
I've run across a problem I'm surprised more people aren't commenting on. If I set a Stop Time (Properties > Details) a minute from the end of a track on a genre with bookmarks enabled, then the bookmark is set to the stop time. This means the next time the track plays, it begins at the very point I wanted it to skip! It should be a simple test: if the bookmark is within a second before the Stop Time, then play from the Start Time instead.
-Christian