This paper provides for new approaches to the processing of unresolved measurements as two direction-of-arrival (DOA) measurements for tracking closely spaced targets rather than the conventional single DOA measurement of the centroid. The measurements of the two-closely spaced targets are merged when the target echoes are not resolved in angle, range, or radial velocity (i.e., Doppler processing). The conditional Cramer Rao lower bound (CRLB) is developed for the DOA estimation of two unresolved Rayleigh targets using a standard monopulse radar. Then the modified CRLB is used to give insight into the boresight pointing for monopulse DOA estimation of two unresolved targets. Monopulse processing is considered for DOA estimation of two unresolved Rayleigh targets with known or estimated relative radar cross section (RCS). The performance of the DOA estimator is studied via Monte Carlo simulations and compared with the modified CRLB.