sure, you can stack anything with anything (and plenty of people do).
Both of those drugs are stong, and are relatively heavy in side effects (in my experience). I personally would not recommend such a stack, expecially if the winstrol is oral, and especially if your fiance is new to the game.
Of those two I would prefer injectable winstrol. If he's new, I recommend starting low, say 100/mg eod. I personally feel some level of test, even 100mg/wk, should be part of the cycle, but I'd then consider dropping the winny back some. Better would be 250mg/wk test and 50mg/eod winny.
I do not recommend using winny for long periods (even with rest between). For me it's very bad for my cholesterol and bladder (very dark to blood in urine).