We present an optimization technique utilizing order statistics with a multichannel digital silicon photomultiplier (MD-SiPM) for timing measurements. Accurate timing measurements are required by 3D rangefinding and time-of-flight positron emission tomography, to name a few applications. We have demonstrated the ability of the MD-SiPM to detect multiple photons, and we verified the advantage of detecting multiple photons assuming incoming photons follow a Gaussian distribution. We have also shown the advantage of utilizing multiple timestamps for estimating time-of-arrivals more accurately. This estimation technique can be widely available in various applications, which have a certain probability density function of incoming photons, such as a scintillator or a laser source.