The invention discloses a detection system of an automatic flexible checking tool based on a contact measuring head, which comprises an adjustable tool, a measuring head seat, the contact measuring head, a controller, software and a main control computer, wherein the system uses the adjustable flexible tool to fix a workpiece and uses a contact measuring head with a communication interface to measure a relative dimension error. The measuring head is mounted on the measuring head seat capable of freely adjusting the gesture of the measuring head. Through the controller, one or more measuring heads are connected with the main control computer which controls the collection and treatment of measured data and realizes the automatic detection of the workpiece error. The system software makes statistic of the measured data, provides the information needed for controlling a statistic process and realizes the self-adapting calibration of the system. The invention has the advantages of good adjustability, low cost, high precision, fast speed, full automation, measures of quantization and the like, is an effective alternative scheme of current manual visual mechanical checking tool, and is also an excellent on-line detection scheme for dimension error of mechanical products.