An operation support system includes an operation data detection unit that detects operation data of a working machine; an operator identification unit that identifies a plurality of operators who operate the working machine; a data accumulation unit that accumulates the operation data and identification information of the plurality of identified operators; a work quality evaluation unit that evaluates work qualities of the plurality of operators and selects the best operator, based on the accumulated data; a learning unit that learns parameters of an operation model of the working machine, based on operation data corresponding to the best operator; and an operation support unit that supports the operators, based on the operation model.