Thanks, I've managed to download and try version 1.3.2 which definitely worked before Catalina and it's failing with the same error.
I have also tried (unsuccessfully) running different versions of wine wrappers, including Windows XP, 7, 8 and 10 to no avail.
Checking the log it seems that this USB error has nothing to do with the application since it happens with classic 1.13c LOD and it manages to run fine, here's the log of a D2 without Sigma:
Exec-ing '"/Applications/CrossOver.app/Contents/SharedSupport/CrossOver/bin/wine" --bottle "D2" --check --wait-children --start "C:/users/crossover/Start Menu/Game.lnk" --cx-log - -w'
001d:err:plugplay:process_IOService_Device object 0x9d03
001d:err:plugplay:process_IOService_Device object 0x6107
001d:err:plugplay:process_IOService_Device Unable to create plug in interface for USB deviceobject 0x610b
0009:fixme:exec:SHELL_execute flags ignored: 0x00000100
0009:fixme:exec:SHELL_execute flags ignored: 0x00004100
Things I've tried so far:
Running wine wrapper in Win XP, 7, 8 and 10 modes.
Running both Diablo II.exe and Game.exe
Running sigma-loader.exe (that's supposed to be used with D2stats)
Running with -w and/or -3dfx flags
Running previous Sigma versions, starting from 1.3.0