Playing with Mathematica, I found that $$\Re\left[\Gamma\left(-\frac{n}{2},x\right)\right]=\Gamma\left(-\frac{n}{2}\right)$$ for $x<0$ and $n$ any positive integer.
Would it be possible to prove that?
On Wikipedia, I found a formula for the incomplete Gamma function when the first argument is a negative integer: $$\Gamma(-n,z)=\frac{1}{n!}\left(\frac{e^{-z}}{z^n}\sum_{k=0}^{n-1}(-1)^k(n-k-1)!z^k+(-1)^k+(-1)^n\Gamma(0,z)\right)$$
Maybe there is a similar formula when the first argument is a negative half-integer!
This is a partial answer I hope will provide a useful starting point. I confirmed the asker's numerical observations with the web version of Mathematica function evalution and the Keisan high-precision calculator. I found a recent paper which gives information in its introduction that also confirms the asker's conjecture:
Ian Thompson, "Algorithm 926: Incomplete Gamma Functions with Negative Arguments", ACM Transactions on Mathematical Software, Volume 39, Issue 2, February 2013, Article No. 14
The referenced equation (3) is the well-known identity $\gamma(a,t)=\Gamma(a)−\Gamma(a,t)$. The paper doesn't go into details as to why $\gamma(n+1/2,-x)$ is always a purely imaginary quantity (at least not in any form that I, as a non-mathematician, recognize as such). It provides the following expansion which may be useful:
$$ \begin{align} S_{n}(x) = e^{-x} \sum_{j=0}^{\infty} \frac{x^{j}}{j!(n+\frac{1}{2}+j)}, \enspace \enspace n \in{}\mathbb{Z}, \enspace x \ge 0, \\ \gamma(n+\frac{1}{2},-x) = i(-1)^{n}e^{x}x^{n+1/2}S_{n}(x). \end{align} $$ It also notes the recurrence relation $$(n+\frac{1}{2})S_{n}(x) + xS_{n+1}(x)=1.$$