This question was asked at the french ENS oral examination. I do not really know how to approach it. I think the answers no.
What I've gathered so far :
Lets call $T$ the subset of $\mathbb{R}^2$ in the title (for obvious reasons). If the union exists, by Baire's theorem it must be uncountable. Let $E$ be the set of maps $T \to \mathbb{R}^2$ of which the images disjointly cover $\mathbb{R}^2$.
Since the domain is compact every map is uniformly continuous : by uncountability, for all $\epsilon > 0$ there is an $\eta$ such that an uncountably infinite number of maps $f$ verify the property $|x - y| \leq \eta \implies |f(x) - f(y)| < \epsilon$.
By uncountability, I also think an uncountably infinite number of the maps above should also have their image in a well chosen compact region of the plane, denoted $K$.
Let $E'$ be an uncoutably infinite subset of $E$ where all the maps verify the two properties ("uniform" uniform continuity and image in a given compact set $K$). For any finite subset of $T$, by using successive extractions I should be able to find a sequence of maps $(f_n)$ in $E'$ such that for any point $x$ in this finite subset the images $f_n(x)$ converges to a point $y \in K$. By using uniform uniform continuity I hoped to find that the maps $f_n$ would be arbitrarily close to one another and necessarily cross.
However, the more I think about this approach the less likely I think it is to work.
Would anyone have an idea ?