A machine failure analyzing system includes a wearable electronic device is for a user to wear, a controlling and processing device provided with a machine history database and a failure causes analyzing unit. When a specific machine is malfunctioning or in a failure status, the controlling and processing device utilizes a machine status data collecting unit to collect machine status data from the specific machine. Subsequently, based on the machine status data, the failure causes analyzing unit is configured to find relative failure causes from the machine history database, thereby generating at least one troubleshooting solution. As such, under instructions of the troubleshooting solution, a field engineer who wears the wearable electronic device can achieve troubleshooting of the specific machine rapidly and precisely, without needing to spend time finding the failure causes.