Compared with Matthew's and Luke's Gospels, Mark has very few points of contact with the Didache. However, there is one parallel of crucial importance for the date of Didache 16 - part of the Didache's earliest layer.

Didache16.8 contains a version of Daniel 7.13 which has been altered to fit the regular structure of the Didache's closing warning about the last days. The alterations in question are highly characteristic of the rest of the warning, so there is good reason to suppose that they are original to this setting. Four of the same changes also appear in the version of Daniel 7.13 used in Mark 13.26. In this case, however, the changes are uncharacteristic of Mark's style and introduce confusion in their new context. This strongly suggests that Mark's text has been influenced by the Didache's reworking of Daniel's prophecy. If this is the case, then Didache 16 predates Mark 13.

Given that there is good reason to suppose that Mark 13 was written before the fall of Jerusalem in AD 70, it follows that Didache 16 comes from a period that is earlier still. For more details see The Gospel of Matthew's Dependence on the Didache pp.191-196.

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