I am attaching photos of my Logitech Gamepad Extreme label so you can compare part numbers. I am also attaching a photo of the gameport-to-USB adapter. The Logitech gameport-to-USB adapter is Logitech Part No. 501269-0000 (marked on the USB connector).
See this thread for information on how to make your own gameport-to-USB adapter (assuming your device is in fact a Logitech Gamepad Extreme). Make sure to read the thread all the way through because you need to short a couple of pins on the gameport side of the adapter in addition to the cross-connector wiring:
https://descentbb.net/viewtopic.php?t=17786
The thread also mentions that you can use a particular Microsoft SideWinder gameport-to-USB adapter as well since it has identical connections to the Logitech adapter.
I hate to say it, but if the WingMan Software does not work with the gameport connection, then the device is likely defective since the WingMan software should work with both the gameport and USB connections. The label should tell you exactly what the device is, and it may just be a WingMan Gamepad which is strictly analog.