Yes. It will truncate the file first, then allocate new blocks for the new random data, likely leaving the old blocks lying around.
You can avoid this with the 'conv=notrunc' option of 'dd'[1]. It will overwrite existing blocks instead of truncating (and possibly reallocating):
notrunc Do not truncate the output file. This will preserve
any blocks in the output file not explicitly written by
dd. The notrunc value is not supported for tapes.
[1]:https://developer.apple.com/library/mac/documentation/Darwin...