Achieving precise control of robotic tool paths is often challenged by inherent system misalignments, unmodeled dynamics, and actuation inaccuracies. This work introduces an Iterative Learning Control (ILC) strategy to enable precise rotational insertion of a tool during robotic surgery, improving penetration efficacy and safety compared to straight insertion tested in subretinal injection. A 4 degree of freedom (DOF) robot manipulator is used, where misalignment of the fourth joint complicates the simple application of needle rotation, motivating an ILC approach that iteratively adjusts joint commands based on positional feedback. The process begins with calibrating the forward kinematics for the chosen surgical tool to achieve higher accuracy, followed by successive ILC iterations guided by Optical Coherence Tomography (OCT) volume scans to measure the error and refine control inputs. Experimental results, tested on subretinal injection tasks on ex vivo pig eyes, show that the optimized trajectory resulted in higher success rates in tissue penetration and subretinal injection compared to straight insertion, demonstrating the effectiveness of ILC in overcoming misalignment challenges. This approach offers potential applications for other high precision robot tasks requiring controlled insertions as well.