There are two sets of coordinates (latitude/longitude) that form a line along the surface area of the Earth. There is a third coordinate, along with a radius, that denotes a circular region somewhere on the surface of the Earth. I need to determine whether or not the given line intersects with that given region.
Example:
Seattle, Washington's coordinates are (47.6062, -122.3321)
Orlando, Florida's coordinates are (28.5383, -81.3792)
Using Haversine's formula, we know that the distance between them is ~2554 miles.
The state of Wyoming has a radius of approximately 150 miles, and the coordinates of its geographic center are (42.5818, -107.4018), putting it in the path of the line from Seattle to Orlando.
First idea : (probably the simplest) Determine the plane of the great circle and the plane of the small circle and determine if their intersection line $L$ is exterior or not to the sphere (for example by testing if the shortest distance of the origin to line $L$ is larger than radius $R$ or not).
Second idea : Use stereographic projection with direct and inverse formulas you will find there.
In this document, it is also established that the image of circles, either great circles or others, are still circles in the projection plane ; your issue becomes a plane (analytical) geometry question : do two circles intersect, and if such is the case, in which points (using in a further step inverse formulas to obtain the spherical coordinates of these points).
There are exceptional cases (circles passing though the pole) that should (and can) be avoided, for example by doing a preliminary rotation that will be compensated later on.