A system and method for analyzing a Web site log file and generating an expanded log file that compensates for information caching and gateway based Web site access. More particularly, the log file expansion procedure of the present invention works with a log file stored in memory on the server computer. The log file contains a sequence of log records, each log record representing an object request by a client computer. Each log record includes data identifying the requested object as well as some data, such as an Internet address, associated with the client computer or a gateway through which the client computer requested the object. The log expansion procedure analyzes the sequence of log records so as to detect object request patterns indicating that object requests not represented by the log records were satisfied by cached object copies, and then supplements the sequence of log records with inserted log records representing object requests for the objects corresponding to the cached object copies. As a result, the supplemented sequence of log records more accurately represents object requests made by client computers than the initial sequence of log records in the log file. Usage metering and analysis procedures utilized the supplemented sequence of log records to generate analysis reports indicative of object request patterns by the client computers.