Yeah it would be fun to imagine...
Maria would still kill him though
I like Maria, but let's get real here...
Kill him? His nickname was "Big" Bill Tilden. Maybe if he was beamed in Star Trek Style direct from the 20s a cold Tilden might, just might lose once to Maria.
But given any amount of practice (or a 3 out of 5 set match) Tilden would be doing the killing my friend.
Exactly how is she going to beat him? Only with power--and any extra power a modern racquet gave her would be balanced by Bill's being a man.
The problem is all the shots she hits for screaming winners against women would be coming back because of Tilden's reach and speed. Have you seen Maria once she has to hit ball after ball after ball? It's why clay is her weakest surface.
And unlike today's top women Tilden would be able to exploit her two-handed backhands with all sorts of slice, or topspin.
He could volley-something she's still improving on.
His serve wouldn't be a puff ball either-he could easily top 100 miles an hour even in those "slow" days. At his best Tilden served with 4 balls in one hand-he would serve 4 aces in a row!
Besides that, he could generate power off of her power.
Put Tilden up against Andy Roddick and he'd get killed, but Maria would get schooled.
The difference between men and women is that big.