Since this is Mojave, the 'mdimport -g' solution that many have proposed doesn't work (not supported).Rebuilt Spotlight index using System Preferences/Spotlight/Privacy - dragging the Outlook Profile folder into it, then deleting it and waiting for it to index again.Checked mdimport -L to make sure that we didn't have 2 instances of Outlook mdimport listed (only 1).Clicked on an email folder in Outlook and used the 'Rebuild' menu choice to reload the emails for just a particular folder.Opened Outlook and added email accounts (imap) and waited for all emails to be processed and for indexing to be completed. Created a new Profile using the Outlook Profile Manager and set it to be the default.Removed Outlook.sqllite file from '~/Library/Group Containers/UBF8T346G9.Office/Outlook/Outlook 15 Profiles/Main Profile/Data' to force an auto rebuild.Used Apple Migration Assistant to migrate data from old 2016 Macbook Pro (in Target Disk mode) to new 2019 Macbook Pro as part of start-up.
Mac Outlook 2016 (version 16.16.12) search returns 'No Results' on new 2019 Macbook Pro (13') running macOS Mojave 10.14.5.