Abstract We present results from long-term monitoring of frequency-dependent eclipses of the radio emission from PSR J1544+4937, which is a black widow spider millisecond pulsar (MSP) in a compact binary system. The majority of such systems often exhibit relatively long-duration radio eclipses caused by ablated material from their companion stars. With the wide spectral bandwidth of the upgraded Giant Metrewave Radio Telescope, we present the first systematic study of temporal variation of eclipse cutoff frequency. With decade-long monitoring of 39 eclipses for PSR J1544+4937, we notice significant changes in the observed cutoff frequency ranging from 343 ± 7 to ≥740 MHz. We also monitored changes in eclipse cutoff frequency on timescales of tens of days and observed a maximum change of ≥315 MHz between observations that were separated by 22 days. In addition, we observed a change of ∼47 MHz in eclipse cutoff frequency between adjacent orbits, i.e., on timescales of ∼2.9 hr. We infer that such changes in the eclipse cutoff frequency depict an eclipse environment for the PSR J1544+4937 system that is dynamically evolving, where, along with the change in electron density, the magnetic field could also be varying. We also report a significant correlation between the eclipse cutoff frequency and the mass-loss rate of the companion. This study provides the first direct evidence of mass-loss rate affecting the frequency-dependent eclipsing in a spider MSP.