Is it possible to enable Supervised Mode on iPhone without a Macbook, through a Windows machine ?

You can use Apple Business Manager or Apple School Manager instead of Apple Configurator.

Get started with a supervised iPhone or iPad - Apple Support

You can also use a 3rd party MDM like Microsoft's Intune to supervise an iPhone. Supervision is mostly used for companies or schools.

https://learn.microsoft.com/en-us/mem/intune/remote-actions/device-supervised-mode

If this is a single device, you probably don't want to setup all the software required for supervision.

Are you sure you want to "supervise" the iPhone?

What exactly are you trying to accomplish?

As I said, seems unnecessary to Supervise devices unless you run a school or business.

Its too complex, just to manage a couple of devices.

You won't really get much more granular control on supervised devices than you can already get form Parental controls and Screen Time.

What exactly are you looking to accomplish by supervising them?

Supervised devices just allows you to quickly deploy them, install apps, and be able to restore them without having the user's Apple ID and password at hand and yes, restrict some settings not available through Parental restrictions, but those restrictions are generally unnecessary in a non corporate or school environment.

Off the top of my head, Always-On tunnels, Activation Lock block, blocking first party apps, bypassing security, disabling iCloud and other first party services. And these things are not not necessary the way Apple has become.

In a supervised device the option of shifting away control of the device from Apple to the supervising entity is very real, which I suspect is the reason why these features aren't available for the general public. But in the Enterprise rules are different, and Apple either complies* or isn't welcome.

*: just barely, or in bad faith, in the name of name of "security" and "privacy," which are really just byproducts of malicious compliance.

Please if you find how to do it come back to post it. Apple Configurator doesn't detect an iPhone, I think it might be too old but I'm not sure. It'd be great if I don't need it to supervise the device. I'll try setting it up in a VM in the meantime. :/

Never mind, it found it finally! :D