I was helping out my neighbor today and she has a 97 Cherokee that gets water on the passenger side floor board when it rains and the vehicle is parked uphill. If she backs into her driveway, no water will accumulate in her rubber floormats. But if she parks facing up the slight incline in her driveway while it's raining it only takes a couple of hours to get an inch on the floorboards. Any idea what would cause that? I pulled back the windshield gasket to check to see if that area is sealing alright and it appears to be doing it's job. I poured a 2 liter of water on her windshield to test it and I didn't see any drips onto the floormat. Could it be something in the cowling? Why only when parked facing uphill?

 

I have the same problem, but it's much less severe, which is why I haven't put forth much effort to figure it out. I believe the water is getting in through the cowling, as you stated. I'm assuming a rotted piece of rubber somewhere in a hard to reach area lol.

 

Does it help if you park at a slight downhill angle?

 

clogged wiper cowl drainnnnnnn