Data Validation List and Vlookup combined

Hey ..

Column H has a drop with list with " Fresh" & " Canc." ( Cancellation ) as two options. 

Column AD has a drop down list depending upon the input in Column C.

So what I want is that incase I select Fresh in Column H, Column ADhas a drop down list but  incase I select Canc.  in Column H there is a VLookup function to lookup for the first occurrence of1111 ( Contract No.) in Column B  and return the corresponding value to it in Column AD in Column AD.  

So basically, what I want is that incase Fresh is selected in Column H, then there is a Drop Down list 

But

Incase Canc. is selected then there is a VLOOKUP function ..

Possible ??