Welcome to the Microsoft Q&A Platform. Thank you for reaching out & I hope you are doing well.
As you are aware, this is not a recommended setup and hence, we will not able to provide a definite answer on the behavior.
Generally, Azure selects a route based on the destination IP address, using the longest prefix match algorithm.
- See : How Azure selects a route
- This means, we can expect that the connection with the longest prefix match should to be preferred over the other.
This behavior may vary and we recommend that you do not have any overlaps
Please let us know if we can be of any further assistance here.
Thanks,
Kapil
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