This one goes way back into my ol' Papel Freelance/Russ Berrie days where we designed novelty gifts. This design was created somewhere around 20 years ago for a Father's Day mug.
The work itself was done by first drawing four pen & ink illustrations. I had to do some old timey library searching for black & white photos to use for reference. Then I needed to create poses that worked well together to create a balanced composition, Once that was done, I took the image, reduced the size, flopped the film and created a repeating pattern in the background. Final stage, everything had to be rubber glued into place on a heavy press board.
I do remember that they liked the design so much, I was "awarded" by having to do another similar design with golfers.