I'm learning vector calculus for the GRE, so this is my first time encountering these concepts. To my knowledge, a gradient field $\mathbf{F}(x,y) : D\to \mathbb{R}^2$ is one where there exists a scalar function $f(x,y) : D\to \mathbb{R}$ such that $$ \mathbf{F}=\nabla f $$ Here, I'm not specifying $D$ to be simply-connected, or even open. I believe this is a valid definition for any subset $D\subset \mathbb{R}^2$.
The fundamental theorem for line integral states that if $\mathbf{F}$ is a gradient field, i.e. $\mathbf{F}=\nabla f$ for some $f$, then along any path $C$ given by the parameterization $\mathbf{r}(t)$ for $a\leq t \leq b$ $$ \int_C \mathbf{F}\cdot d\mathbf{r}= f(\mathbf{r}(b))- f(\mathbf{r}(a)) $$
This might be a dumb question, but what if the domain has holes?
For example, take the scalar function $$f(x,y) = \frac{xy}{x^2+y^2}$$ then the corresponding gradient field is $\mathbf{F}(x,y) = \left( \frac{y(y^2-x^2)}{(x^2+y^2)^2}, \frac{x(x^2-y^2)}{(x^2+y^2)^2} \right)$.
I tried to take the line integral over the upper half circle, and the lower half circle, and it turns out they are both zero. Could I have applied the fundamental theorem of line integrals to this vector field $\mathbf{F}$?
Yes you could have use the theorem. If you take a look at the short proof of the theorem,
\begin{align*} \int_C \mathbf{F}\cdot d\mathbf{r} &= \int_a^b \mathbf{F} (\mathbf{r} (t)) \mathbf{r}'(t) dt\\ &= \int_a^b\nabla f (\mathbf{r} (t)) \mathbf{r}'(t) dt \\ &= \int_a^b \frac{d}{dt} (f\circ \mathbf{r})(t) dt\\ &= (f\circ \mathbf{r})(b)-(f\circ \mathbf{r})(a). \end{align*}
We used only chain rule and the standard fundamental theorem of calculus. No assumptions about the domain $D$ (besides that the curve $C$ lies inside $D$).