In one aspect, a system for regulating the operating distance defined between work vehicles during the performance of field operations may include a sensor configured to emit an output signal for reflection off of a component of a first work vehicle or a second work vehicle and detect the reflected output signal as a return signal. A controller of the system may be configured to monitor an operating distance between the first and second work vehicles within the field based on data received from the sensor associated with at least one of the output signal or the return signal. Additionally, the controller may be configured to initiate a control action associated with adjusting a relative positioning between the first and second work vehicles within the field when it is determined that the monitored operating distance has fallen outside the predetermined operating distance range.
