The accuracy and fluency of a handover task affects the work efficiency of human–robot collaboration. A precise and proactive estimation of handover time points by robots when handing over assembly parts to humans can minimize waiting times and maximize efficiency. This study investigated and compared the cycle time, waiting time, and operators’ subjective preference of a human–robot collaborative assembly task when three handover prediction models were applied: traditional method-time measurement (MTM), Kalman filter, and trigger sensor approaches. The scenarios of a general repetitive assembly task and repetitive assembly under a learning curve were investigated. The results revealed that both the Kalman filter prediction model and the trigger sensor method were superior to the MTM fixed-time model in both scenarios in terms of cycle time and subjective preference. The Kalman filter prediction model could adjust the handover timing according to the operator’s current speed and reduce the waiting time of the robot and operator, thereby improving the subjective preference of the operator. Moreover, the trigger sensor method’s inherent flexibility concerning random single interruptions on the operator’s side earned it the highest scores in the satisfaction assessment.