The answer is "no" if you mean that these matrices correspond to a fixed choice of basis.
I will build a counterexample for the case of $q = 2, n = 3$. Note that all maps of the form $T_\alpha$ for $\alpha \in \Bbb F_{2^3}$ commute. Thus, if we find an $\alpha \in \Bbb F_{2^3}$ and a matrix $M \in \Bbb F_2^{3 \times 3}$ such that $M^7 = I$ (since $q^n - 1 = 7$) but $MT_{\alpha} \neq T_\alpha M$, then we have found an $M$ that cannot be realized as a Singer cycle.
Present $\Bbb F_8$ as $\Bbb F_2[x]/\langle x^3+x+1 \rangle$. Then relative to the basis $\mathcal B = \{1,x,x^2\}$ of $\Bbb F$, the matrix of $T_{x}$ is given by
$$
[T_x]_{\mathcal B} = \pmatrix{0&0&1\\
1&0&1\\
0&1&0}.
$$
Because $x$ is a primitive element, $T_x$ has order $7$. This matrix fails to commute with its transpose, $M = ([T_x]_{\mathcal B})^\top$. However, $M$ must have the same order as $T_x$. Thus, $M$ is a matrix of order $q^n - 1$ that does not correspond to a singer cycle (relative to this basis $\mathcal B$).
For posterity: we find that
$$
[T_x]_{\mathcal B}([T_x]_{\mathcal B})^\top = \pmatrix{1&1&0\\1&0&0\\
0&0&1},\\
([T_x]_{\mathcal B})^\top[T_x]_{\mathcal B} = \pmatrix{1&0&1\\0&1&0\\
1&0&0}.
$$
It is notable that two matrices of maximal order need not even be conjugate to each other. As counterexample to this, consider $[T_x]_{\mathcal B}$ as above and the matrix
$$
M = \pmatrix{0&0&1\\1&0&0\\0&1&1},
$$
which also has order $7$. We can see that these matrices are not conjugate since they have characteristic polynomials $x^3 + x + 1$ and $x^3 + x^2 + 1$ respectively.
Regarding the project of counting elements of $GL_n(\Bbb F_q)$ of maximal order, I would note the following for the case that $q$ is prime.
It is known that the cyclotomic polynomial $\Phi_{q^n - 1}(x)$ factors into a product of irreducible polynomials of the same degree, which (given the existence of primitive elements) must be of degree $n$. Each of the $\varphi(q^n - 1)/n$ factors (that I believe are distinct) are a possible candidate for the characteristic (and minimal) polynomial of a matrix in $GL_n(\Bbb F_q)$. In other words matrix with maximal order must be conjugate to the companion matrix associated with one of these polynomials.
With that, the process of selecting a matrix of maximal order can be broken down to selecting a factor of $\Phi_n$, then selecting a matrix that is conjugate to the associated companion matrix.
As for counting the elements conjugate to a given companion matrix $C$, the following argument works.
Consider the action of $GL_n(\Bbb F_q)$ on itself given by conjugation, i.e. the action $A \cdot X = AXA^{-1}$.
- The matrix $C$ is non-derogatory, which means that $A$ is in the stabilizer of $C$ if and only if $A = f(C)$ for some polynomial $f$.
- The non-zero matrices of the form $f(C)$ for such a polynomial form a subgroup of $GL_n(\Bbb F_q)$ that is isomorphic to the multiplicative group of $\Bbb F_{q^n}$. Thus, $GL_n(\Bbb F_q)_C$, the stabilizer subgroup of $C$ has order $q^n - 1$.
- By the orbit stabilizer theorem, the number of distinct elements conjugate to $C$ is given by
$$
\frac{|GL_n(\Bbb F_q)|}{|GL_n(\Bbb F_q)_C|} = \frac{(q^n - 1)(q^n - q)\cdots (q^n - q^{n-1})}{q^n - 1} = (q^n - q)\cdots (q^n - q^{n-1}).
$$
Putting the previous two sections together, we have a potential answer for prime values of $q$. If we accept the hypothesis that $\Phi_{q^n - 1}$ has no repeating factors, then the total number of distinct matrices in $GL_n(\Bbb F_q)$ with order $q^n - 1$ is given by
$$
\frac{\varphi(q^n - 1)}{n} \cdot (q^n - q)\cdots (q^n - q^{n-1}).
$$
Equivalently, the fraction of elements of $GL_n(\Bbb F_q)$ that have maximal order is
$$
\frac{\varphi(q^n - 1)}{n\cdot (q^n - 1)}.
$$