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Outlook for Mac 2019 - Search not working :-(
Due to some changes in macOS Mojave, the OutlookSearchRepair tool no longer works in 10.14 and higher. If you are on macOS Mojave (10.14), you can follow the steps below to reindex Spotlight for Outlook for Mac.
Choose Apple menu, then System Preferences, and then Spotlight.
Select the Privacy tab.
In Finder:
On the Go menu, select Go to Folder...
Copy and paste the following location into the "Go to the folder:" dialog box and select Go:
~/Library/Group Containers/UBF8T346G9.Office/Outlook/Outlook 15 Profiles/
Drag the "Main Profile" folder to the Privacy tab. Once added, remove the folder, and Spotlight will re-index the folder.
You must perform this step for any additional profile folders you have.
See the following article from Apple to learn more: https://support.apple.com/HT201716.