$a\div b\,$ has remainder $\,r\,$ means $\,a = q\,b + r\,$ for some quotient $q\in\Bbb Z,\,$ where the remainder $\,r\,$ is normalized to be unique by some convention, i.e. $\,r\,$ must lie in a fixed complete set of remainders - usually the set $\,\color{#0a0}{0\le r< b},\,$ but another common choice is least magnitude reps, e.g. the remainders $\,\color{#c00}{0,\pm1,\pm2}\pmod{\!5}.\,$ In the latter case we do have negative remainders, e.g. in your mentioned case we have $\,a\div 5\,$ has remainder $\,-1\iff a = 5\,q - 1,\,$ e.g.
$$\begin{align} -6 &\,=\, 5(-1)-\!1\\ \color{#c00}{-1} &\,=\, 5\cdot 0\ -\ 1\\ \color{#0a0}4 &\,=\, 5\cdot 1\ -\ 1\\ 9 &\,=\, 5\cdot 2\ -\ 1\end{align}\qquad $$
So $\,-6,-1,4,9\,$ have remainder $\,\color{#c00}{-1}\,$ using least magnitude reps vs. remainder $\,\color{#0a0}4\,$ with usual reps.
As for $\, -1\div b\,$ having remainder $\,1,\,$ it means $\,\exists\, q\!:\, {-}1 = q\,b + 1\! \iff\! \exists\,q\!:\ q\,b = -2\!\iff\! b\mid 2,\,$ hence it is true iff the divisor $\, b = \pm2\,$ or $\,\pm1,\,$ and $\,1\,$ lies in our chosen normal set of remainders.
That said, it is usually more convenient to work with congruences rather than normalized remainders since congruences are more compatible with arithmetic (see Congruence Rules) and they give us the flexibility to vary the choice of remainder rep as we like - choosing what is most convenient in any context. For example when casting out elevens it is more convenient to choose the rep $-1\,$ from the congruence class $\,10+11\Bbb Z\,$ when computing $10^n\equiv (-1)^n\pmod{\!11}$. This is analogous to having the flexibility to work with fractions that are not normalized (i.e. not reduced to lowest terms), e.g. the fraction addition rule is stated most simply by scaling them to have a common denominator (which generally yields non-reduced fractions). It would be very inconvenient if we always had to work with reduced fractions - just like it is inconvenient to compute $10^n$ vs. $(-1)^n$ when casting out elevens.