[[Similar issue here. User with a 2010 Apple Cinema display, which involves three connectors: USBc for power, USB a>c adapter for a/v, and a UPTab USB-C Type C to Mini DisplayPort Adapter. As the user stated, it's not pretty, but it worked up until the 10.15.4 update.]]
I have the exact same situation. Although the Cinema Display is from 2010, it has only been used sparingly for the past 2 years and sat in the original box until 2018. I have a MacBook Pro from 12/2018 and the external Cinema Display was working perfectly up until the Catalina 10.15.4 update. I have tried a number of things I found online, including resetting the SMC, resetting the NVRAM, and starting in safe-mode, and then restarting. Also tried pressing Ctrl-F2 after each reboot; unplug/plug the monitor; swapped external usb-c connections around. During this time I was lucky enough to get the display to be detected by the system, however, once the display is disconnected again the problem reoccurs. Currently stuck trying to get it to work again - no luck so far. I opened an issue with Apple support - phone support stated that they would call back is an estimated 2 minutes wait - the call came in very late at night but I was unable to answer the phone in time before the auto caller hung up. I will be trying again since I now have a case#. Here is the Software version info for my machine, looks like I am at the latest upgrade, maybe it will be of help to someone:
System Software Overview:
System Version: macOS 10.15.4 (19E287)
Kernel Version: Darwin 19.4.0
Boot Volume: Macintosh HD