Vigorous particle collisions and mechanical processes occurring during high-velocity pneumatic conveying often lead to particle degradation. The resulting particle size reduction and particle number increase will impact on the flow characteristics, and subsequently affect the electrostatic type of flow measurements. This study investigates this phenomenon using both experimental and numerical methods. Particle degradation was induced experimentally by recursively conveying the fillite material within a pneumatic pipeline. The associated particle size reduction was monitored. Three electrostatic sensors were embedded along the pipeline to monitor the flow. The results indicated a decreasing trend in the electrostatic sensor outputs with decreasing particle size, which suggested the attenuation of the flow velocity fluctuation. This trend was more apparent at higher conveying velocities, which suggested that more severe particle degradation occurred under these conditions. Coupled computational fluid dynamics and discrete element methods (CFD–DEM) analysis was used to qualitatively validate these experimental results. The numerical results suggested that smaller particles exhibited lower flow velocity fluctuations, which was consistent with the observed experimental results. These findings provide important information for the accurate application of electrostatic measurement devices in pneumatic conveyors.