If I would seriously wager anything, I would say yes, I think I can win a few points vs a top 100 player, a complete match could possibly be 2-4 points won by me vs 48 won by him.
I'm taking a group class over here, the teaching pro just turned 40, he won some ATP points a long time ago, somo other teaching pro told me he was a good prospect that the only thing keeping him from really breaking into the top 1000 ranking was his temper, he used to break racquets too often and his dad told him he would retire his support unless he changed, he didn't and his dad had to fulfill his threat.
This teaching pro sometimes plays with us, you can see that he's toying with us, the best shot from me, one that normally would be a winner is too easy to get for him, he can rip winner from anywhere in the court and Ive had many rallies where I'm playing totally focused, high speed balls and for me those are high level, for him are almost neutral balls, he then would decide he wants to balst a winner and simply does it, it is akin to me playing with a child, the gap is simply too wide to comprehend, if he played me in a match, I'm certain he would win easily almost every point easily, I could count on him making an unforced error now and then and on me forcing an error maybe 3 or 4 times per set.
With a top 100 player any 5.0 would look like a 2.0 looks to a 5.0.