I'm trying to find the behaviour at large $t$ of solutions to the non-linear differential equation: $$\dfrac{d^2y}{dt^2}-\left(\dfrac{dy}{dt}\right)^2+(2-a)t\dfrac{dy}{dt}+2ay=0$$ I tried to replicate the approach detailed on Wikipedia, making the assumption that $y(t)\sim e^{S(t)}$ as $t\to\infty$ for some function $S(t)$, but the $\left(\dfrac{dy}{dt}\right)^2$ term in the DE leaves me with an extra factor of $e^{S(t)}$ that I don't know how to deal with.
How do I go about finding the asymptotic series for $y(t)$?

The assumption $y \sim \exp S$ is the way to go if the highest derivative is multiplied with a small factor.
For your problem, the correct approach is to single out the (two or more) terms that dominate the others for $t\to\infty$. Which terms this are is a bit trial and error (and some experience).
You did not specify what values of $a$ you are interested in (the analysis depends on that). I assume for the following that $0<a<2$. If you are interested in other values, please just comment and I will edit the answer.
We claim that the solution to $$ (2-a) t y'(t) +2a y(t)=0$$ gives the correct asymptotic expression for $t\to\infty$. We obtain the solution $$y(t) \sim c t^{-a/(1-a/2)}.$$ We observe that $$ \lim_{t\to\infty} \frac{y'^2}{y} = \text{const} \lim_{t\to\infty} t^{-4/(2-a)}=0 $$ and $$ \lim_{t\to\infty} \frac{y''}{y} = \text{const} \lim_{t\to\infty} t^{-2}=0 $$ and thus the remaining terms are subdominant and we have obtained the correct asymptotic solution.
Appendum:
Due to the request of the OP, I add the analysis for $a>2$ in the following: this is a untypical case as we need to keep three terms of the differential equation. We note that with $y(t) \sim \alpha t^2$, we have that $y''(t) \ll y(t)$. Thus the differential equation is given by $$0 =-y'^2 +(2-a) t y' +2a y = 4 (1-\alpha) \alpha t^2.$$ With the solutions $\alpha_0\in\{0,1\}$ (only $\alpha_0=1$ makes sense as otherwise the solution is not behaving like $t^2$)
We try to obtain a better estimate and substitute $y(t) = t^2 + \epsilon(t)$. We obtain the new equation $$2 + 2a \epsilon -(2+a) t \epsilon'- \epsilon'^2 + \epsilon'' =0.$$ The dominating terms for $t\to\infty$ are given by $$2a \epsilon-(2+a) t \epsilon' =0$$ which can be explicitly checked. The solution (for $a>2$) is thus asymptotically given by $$ y(t) \sim t^2 + c t^{a/(a/2+1)}$$ with an constant $c$.
The asymptotic expansion is of course only valid for a certain set of initial conditions such that the solution does not diverge before. From numerics (see Robert Israels anwer), it seems that the solution is unstable; meaning that closeby trajectories will actually move away from the asymptotic result given above. As such, the curve $y(t)=t^2$ seems to serve as a separatrix.
However to see that the result is correct, it is best to integrate the equation backwards (from large to small times). Below, I give results for the initial problem $$ y(10^3) =10^6 +10^5, \qquad y'(10^3) = 0$$ close to $y(t)\sim t^2$.
We have (blue numerical result, orange $t^2$)
Subtracting $t^2$, we obtain the subdominant term $t^{a/(a/2+1)}=t^{6/5}$ (blue $y_\text{numeric}(t) -t^2$, orange $10 t^{6/5}$)