In this paper, we present a time-to-digital converter (TDC)-based maximum delay sensor (MDS) for on-line timing error detection in the logic block of very large scale integration (VLSI) circuits. The MDS captured the maximum propagation delay of the target end point for on-line timing error detection. Because the MDS was TDC-based, the resolution was high. In addition, the periodic on-line maximum delay capturing for on-line timing error detection using an MDS did not interrupt normal operation. Because the MDS was a small digital circuit, it could be easily inserted into the logic blocks of high-speed and low-power processors and systems-on-chip (SOCs). With LTSPICE simulation using 45 nm metal gate/high-K/strained-Si of the predictive technology model, the behavior of the proposed analyzer was confirmed. The results showed that the area overhead is 34.9% on average.