[Wine] Hawkes intermediate algebra

[Tinkrtrain]

Does anyone have a clue if the latest version of Wine will run Hawkes Learning System for intermediate algebra?

The test data for this application is very old from what I can see.

My nephew recently purchased a macbook for school and they instantly hit him with a ridiculous program that is only windows based.  So I would love to use Wine vs. buying a copy of windows and have him his virtualbox. 

Any help or knowledge would be greatly appreciated, as I am severely lacking in Mac knowledge.

thanks

-Tink