That particular exact streak of 20 specific numbers? That’s easy: 1 in 20^20, which is a very large number. But that’s the wrong question to ask, because the answer is the same for any sequence of 20 rolls.
The better question to ask is what are the odds of having a result that is at least as remarkable as the one observed, or more. This one is a little tricky, because it depends on how you define “remarkable”.
For the sake of argument, I’ll consider “remarkability” based on the sum of those numbers (in other words, treat it as a single roll of 20d20). His total roll is 302, while the average of 20d20 is 210. So he’s definitely above average.
But how much above average? Well, when you’re throwing that many dice, your results will be very well approximated by a normal distribution. We already know the average of this distribution, so we just need to know the standard deviation, and we’ll know everything about the distribution. The standard deviation is the square root of a quantity called the variance, and the variance of a sum of dice rolls is just the sum of the variances of the individual rolls. A single roll of an n-sided die, meanwhile, has a variance of (n^2 - 1)/12. Thus, a single d20 roll has a variance of 399/12 or 33.25, and 20d20 has a variance of 665. The square root of 665 is about 25.79 , meaning that’s the standard deviation (we can also write this as the distribution being 210 ± 25.79). His rolls are 92 higher than the average, which is 3.57 standard deviations.
Using a cumulative probability calculator or a standard table, we find that the result has a .99982 chance of being less extreme than that, or a 0.00018 chance (1 in over 5500) of being that extreme or more.
Which still doesn’t necessarily mean anything. That’s the chance of any one streak of 20 rolls to be that good. But you’ve seen many, many streaks of 20 rolls before, and the ones that weren’t remarkable, you never bothered to ask about. How many such streaks have you seen? Well, how many people do you game with, how often do you meet, and for how long have you been meeting? If you’ve got 10 people in your group, for instance, and you’ve met every week for the past decade, then you’d expect that at some point in your gaming history, you’d get about one streak that good. Cut it down to half that many people at half that many events, and it’s still not particularly surprising.