Hello & Welcome to JustAnswer. Where were these contacts saved initially and would you like me to connect remotely to check / troubleshoot this directly?
When you re-opened Outlook after upgrade did it contain previous emails? Are the contacts saved on your iPhone?
Okay. Can you sync your contacts to iCloud from your iPhone?
Please login to www.icloud.com and see if you can see your contacts there from your computer.
Let me know
Rest is easy; please follow the steps here to sync iCloud contacts with Outlook: If you want me to perform the steps at the link for you and set this up; then i have sent you an offer of remote assistance (which will ensure that i do it correctly for you to get you up and running) otherwise, the steps are pretty easy to follow.http://www.slipstick.com/outlook/icloud-and-outlook-problems/
Take your time.