Basically, a dead end. To understand why, you need to look at how Wine and Windows work.

Microsoft Windows runs on computers with an Intel processor (8086, 80286, 80386, 80486, and the rest of it, generally known as "i86" even though now they're officially called "Pentium", "Celeron" etc.). They also run on AMD chips because AMD chips were built to run just like Intel chips.

Compare this to Linux, which runs on a much wider variety of processors including i86, the Motorola 68000/ 68020/ 68030 that used to power the Macs until they transitioned to Intel chips.

If you try to run Windows programs on a Motorola (or other non-Intel-type) processor, it fails completely since it's a completely different chip with different instruction sets.

If you try to run Windows programs on an Intel processor, but not using MS Windows, it would fail only because there is no MS WIndows running, but the chip is correct and you just have to supply the correct support software to talk to the program you're running. That's what Wine does.

Here's another analogy: running Windows programs on Linux on an Intel machine is like trying to perform a stage play, the actors/actresses cannot get to the stage because the doors to the theatre are locked.

Running Windows programs on a non-Intel machine like an ARM processor is like trying to perform a stage play when you're not in a theatre, and you're not even in a city --in fact, you're not even on land but knee deep in the middle of a river.

So, yeah, dead end.

As others suggested, you could try Windows CE, but not sure if Wine supports WinCE or what. But all this stuff about "well, just make it run on very small, short, simple programs" --naah, ain't gonna fly very far there.