Upgrade CUCM 9.x to 14

Thank you Timothy for your advice/insight.

If we have 14 licenses purchased, do we just ask cisco for the 10 iso and cop files , etc?

We have a brand new Dell host for all our VMs that we will be migrating to as well.

The info from the link for 10 to 14 shows no need for COP files.

Looking for the info on how to get from 9.x to 10 and the associated cop files

I almost forgot, the upgrade(s) are going to take quite some time. You're going to stare at the upgrade screen for quite some time.
And... shame on whoever is responsible for letting this CUCM get this far behind. 9.1 has a final end of support date of 12/31/2018. :(
Also, have you considered the issued you are going to face with Unity Connection? There are some things you can do with COBRAS to help with that. 

What issues do you forsee with Unity? all the call flow is handled with Unity Auto-attendants so it is very dependant on it.

You need Cisco or a Cisco Partner to provide the ISOs and necessary COPs, and OVAs. 

the only iso I see on Cisco's site after logging in, is 10.0.1.10000-24-recovery.iso , will this work for the upgrade?

there are some OVA templates but they are only .35Mb in size

I've use the Cisco provided and TAC supported COBRAS tool for Unity Connection upgrades like this. With COBRAs, you can "suitcase" a Unity Connection database on a (usually on a virtual machine) and un-suitcase it on the new Unity Connection, no need to upgrade the CUC box then. There are some version dependencies, but I haven't seen one in while.
BTW, 14 is VERY new, I'm not a fan of the bleeding edge. 12.5 is pretty mature, (there is no 13) YMMV.
You are probably going to need temp licenses, since I'm pretty sure that you can't upgrade a non-licensed CUCM.  

Any sub version of 10.0 will count as 10.0 for upgrade dependency purposes. so you'll be fine with that version.
The OVAs are only OVAs (templates), they don't contain the OS or anything else, they just define the CPU(s), affinity, RAM, disk space etc. I HIGHLY suggest using the Cisco provided OVAs, in fact Cisco TAC also doesn't like to support "non-OVA build VMs of CUCM/CUC, etc..."

For upgrade planning, this page is your friend.
https://www.cisco.com/c/en/us/support/unified-communications/unified-communications-manager-callmanager/products-installation-guides-list.html
You'll find the 10.0 upgrade guide at the bottom. 

Thank you very much Timothy for all of this valuable advice......this gives me a great baseline to start planning with.

Going to close this out. I am sure I will have more questions once I start to move forward.

Excellent! Glad I could help.

Strong knowledge in Cisco Voice