Connecting 27" Cinema Display to Macbook Pro booted to Windows

Item #1 is to suggest your 2014 MacBook Pro can easily

be upgraded to Catalina 10.15.7; &/or Big Sur macOS11.x

Item #2 for Windows 10 w/ Apple 27-inch Cinema display?

Hard to say, my 20-inch Apple Cinema (aluminum)

expects me to find workability through BootCamp.

Few issues may negate Thunderbolt in that configuration.

But check on the actual final upgrade for macOS.

(How to) Get old versions of macOS - Apple Support

• macOS Big Sur is compatible with these computers - Apple Support

https://support.apple.com/en-us/HT211238

• macOS Catalina is compatible with these computers - Apple Support

https://support.apple.com/en-us/HT210222

iWould doubt if your MacBook Pro could handle Monterey macOS12.

Learn how to upgrade to macOS Monterey, the latest version of macOS.

Some times a firmware or other invisible file which accompanies a major macOS version,

changes how those download installers are seen by the Mac; so that's what I figure; more

of those have that only work, when parts are visible to the Mac.

[A few upgrade steps to a system on one of my server's internal HDDs, allowed me to

see and locate recent yet invisible systems upgrades that had remained invisible. So

that Mac has duplicate download installers(?) And a firmware added newer abilities.]

Certain upgrades are required, before others could be used, or seen; in some instance.

Glad your system configuration is now finding what it already has nearby!

Take care & safe travels! ☃️❄️🌿🍁