Hi,
the answer is:
"Longest match wins."
I.e., it should be no problem on a Cisco router to route 10.199.0.0/16 to one next-hop A and 10.0.0.0/8 to another next-hop B.
As longest match wins, everything should work fine, the whole 10.0.0.0/8 would be routerd to B with the exception of 10.199.0.0/16 routed to A.
I've met some non-Cisco devices which did not accept this rule, but never had a problem with this on Cisco.
BR,
Milan