Is it possible using mathematics that is not much beyond high school mathematics to prove that special relativity is wrong? And what does that even mean?

The mathematics of special relativity
It is more-or-less true that Einstein’s original works on special relativity do not really use any highbrow mathematics. In a standard undergraduate introduction to the subject no more than linear algebra is really used: vector spaces, matrices and quadratic forms.

So, as linear algebra is well-founded, one is not going to find some internal inconsistencies in special relativity.

Moreover, today we understand special relativity to be based on the geometry of Minkowski space-time. Basically, this is Euclidean with an awkward minus sign in the metric. Thus, special relativity, from a geometric perspective, is as well-founded as any thing in differential geometry.

So one is not going to mathematically prove that special relativity is wrong in any mathematical sense.

On to physics…
However, the theory of special relativity is falsifiable in the sense of Popper. That is, taking into account the domain of validity (ie., just the situations you expect the theory to work), experimental accuracy, statistical errors etc. one can compare the theoretical predictions with what is measured in experiments. If the predictions match the theory well, up to some pre-described level, then the theory is said to be ‘good’. Otherwise the theory is ‘bad’ and not considered to be a viable description of nature.

In this sense, using not much more that linear algebra one could in principle calculate something within special relativity that does not agree well with nature (being careful with the domain of validity etc). Thus, one can in principle show that special relativity is not a ‘good’ theory by finding some mismatch between the theory and observations. This must be the case if we want to consider special relativity as a scientific theory.

Is special relativity ‘good’ or ‘bad’?
Today we have no evidence, direct or indirect, to suggest that special relativity is not a viable description of nature (as ever taking into account the domain of validity). For example, the standard model of particle physics has at its heart special relativity. So far we have had great agreement with theory and experiment, the electromagnetic sector is extremely well tested. This tells us that special relativity is ‘good’.

Even the more strange predictions like time dilation are realised. For example the difference in the life-time of muons as measured at rest and at high speed via cosmic rays agrees very well with the predictions of special relativity.

Including gravity into the mix produces general relativity. However, we know that on small enough scales general relativity reduces to special relativity. Any evidence that general relativity is a ‘good’ theory also indirectly tells us that special relativity is ‘good’. Apart from all the other tests, I offer the discovery of gravitational waves as evidence that general relativity is ‘good’ and thus special relativity is also ‘good’.

The clause
The important thing to remember is that the domain of validity is vital in deciding if a theory is ‘good’ or ‘bad’. We know that physics depends on the scales at which you observe, so we in no way would expect special relativity be a viable description across all scales. For example, when gravity comes into play we have to consider general relativity.

On the very smallest length scales, outside of what we can probe, we expect the nature of space-time to be modified to take into account quantum mechanics. Thus, at these smallest length scales we would not expect the description of space-time using special relativity to be a very accurate one. So, no one is claiming that special relativity, nor general relativity is the final say on the structure of space and time. All we are claiming is that we do have ‘good’ theories by the widely accepted definition.

Are all claims that relativity is wrong bogus?
Well, one would have to examine all claims carefully to answer that…

However, in my experience most objections to special relativity are based on either philosophical grounds or misinterpreting the calculations. Neither of these are enough to claim that Einstein was completely wrong in regards to relativity.