Four cylindrical sandstone samples were extracted from the original rectangular sample with a rough-walled fracture. Each drilling angle (θ) of cylindrical sandstone samples is different to consider the anisotropies of rough-walled rock fractures. For each sample, different flow velocities ranging from 0 m/s to 13 m/s were designed. For a given flow velocity, a series of different confining pressures (
σ
n
), including 1.5 MPa, 2.5 MPa, and 3.5 MPa, were applied on the fractured samples. The hydraulic properties of each cylindrical sandstone sample were tested under different shear displacements (
u
s
) and
σ
n
. The results show that the hydraulic gradient (
J
) shows an increasing trend with the increment of
σ
n
. With the increment of the Reynolds number (
Re
), the transmissivity (
T
) decreases in the form of the quadratic function. The normalized transmissivity (
T
/
T
0
) decreases with the increment of
J
. The variations in
T
/
T
0
with
J
can be divided into three stages. The first stage is that
T
/
T
0
approximately holds a constant value of 1.0 when
J
is small indicating that the fluid flow is in the linear regime. The last two stages are that
T
/
T
0
decreases with the continuous increase of
J
, and the reduction rate first increases and then decreases. The critical Reynolds’ number (
Re
c
) of the sample angle with a drilling angle of 90° is different from that of other samples. The corresponding
Re
c
is 6.52, 28.73, and 32.1 when the shear displacement
u
s
=
2
mm
, 3 mm, and 4 mm, respectively. The variations in
Re
c
and
J
along different drilling angles are significantly obvious. When the confining pressure is large, the effect of anisotropy on Rec is much greater than that of confining pressure.