Who would win and why?
Can jackie avoid the penance stare and can he withstand Ghost Rider's hellfire attack?
VS AND DEFEATING DOCTOR STRANGE:
Dr. Strange's explanation of Ghost Rider's "godlike" powers :
I'd go with Ghost Rider he did kill Black Heart after all and Estacado would not have been a match for Black Heart. The Darkness is a relatively new comic character who has probably been inspired by the likes of Black Heart, who seems to have the same abilities and more. Black Heart summoned demons, could alter his size, travel in and out of dimensions, spiritual plains and Ghost Rider crushed his skull in anger. I can't help but think Ghost Rider is being hugely underestimated here.
If Ghost Rider can kill Black Heart he can defeat Estacado. The Darkness can't be killed but without Estacado there would be no darkness in our plain(Earthly realm). Estacado isn't a demon like Black Heart, he's a man with emotions, capable feeling guilt and fear. Penance stare would see that Estacado didn't come back. He would be reduced to ash and with out a soul, incapable of returning from death to host the darkness.