You can't play MKV files with iTunes as MKV is not the supported format of iTunes. The best solution is to convert MKV to iTunes compatible formats such as MP4 or M4V, and then you can add MKV to iTunes Library and playback without trouble.
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6 Jun 2019 If you added some MKV files to iTunes library but nothing shows up, the MKV movie in iTunes, we have to convert MKV to iTunes compatible