Abstract We describe a new transit-detection algorithm designed to detect single-transit events in discontinuous Perkins INfrared Exosatellite Survey (PINES) observations of L and T dwarfs. We use this algorithm to search for transits in 131 PINES light curves and identify two transit candidates: 2MASS J18212815+1414010 (2MASS J1821+1414) and 2MASS J08350622+1953050 (2MASS J0835+1953). We disfavor 2MASS J1821+1414 as a genuine transit candidate due to the known variability properties of the source. We cannot rule out the planetary nature of 2MASS J0835+1953's candidate event and perform follow-up observations in an attempt to recover a second transit. A repeat event has yet to be observed, but these observations suggest that target variability is an unlikely cause of the candidate transit. We perform a Markov Chain Monte Carlo simulation of the light curve and estimate a planet radius ranging from 4.2 − 1.6 + 3.5 R ⊕ to 5.8 − 2.1 + 4.8 R ⊕ , depending on the host’s age. Finally, we perform an injection and recovery simulation on our light-curve sample. We inject planets into our data using measured M-dwarf planet occurrence rates and attempt to recover them using our transit-search algorithm. Our detection rates suggest that, assuming M-dwarf planet occurrence rates, we should have roughly a 1% chance of detecting a candidate that could cause the transit depth we observe for 2MASS J0835+1953. If 2MASS J0835+1953 b is confirmed, it would suggest an enhancement in the occurrence of short-period planets around L and T dwarfs in comparison to M dwarfs, which would challenge predictions from planet formation models.