A trail management system acquires and manages operation contents in a PC that is provided with an operation function including a document transcription function. When a user performs a transcription operation, a server acquires operation information and stores it as chronological data. The operation information contains time of the transcription operation, a user name, a value transcribed by the transcription operation, document specification information for specifying a transcription origin document during the transcription operation, location specification information for specifying a transcription origin location in the transcription origin document, document specification information for specifying a transcription destination document during the transcription operation, and location specification information for specifying a transcription destination location in the transcription origin document. Using a PC, an administrator searches for chronological data in accordance with a search condition supplied to search for the chronological data and displays a search result on the PC.