We study a pilot scheduling and assignment problem (PSAP) to vessel transiting the St. Lawrence River considering different measures to rank the pilots to be assigned over four different pilot stations along the maritime corridor while it typically happens once in the port at previous works. To do this end, two different strategies are explored; the current approach and a new one. The current strategy applies the number of pilotage and waiting time as a pilot satisfaction level factor while the proposed strategy combines nine different measures including working time, waiting time, and skill difference as pilot satisfaction level factor. A case study based on the context of the St. Lawrence River from Les-Escoumins to Montréal is used. The results show the standard deviation value obtained by the proposed strategies is reduced in all measure, as a result, the new proposed approach makes a more balanced schedule for pilots.