A data management system is disclosed for use with a plurality of machines operating at a worksite. The data management system may have a plurality of onboard sensory devices, each configured to generate data regarding at least one of machine performance and worksite conditions. The data management system may also have a plurality of onboard locating devices, each configured to generate a machine location signal. The data management system may further have a plurality of onboard communication devices, and a worksite controller. The worksite controller may be configured to receive the data and the machine location signals from onboard the plurality of machines via the plurality of communication devices, trigger an event based on the data received from onboard at least a first of the plurality of machines, and selectively retrieve data from at least a second of the plurality of machines based on event triggering.