Timing synchronization (TS) is vital for orthogonal frequency division multiplexing (OFDM) systems, which makes the discrete Fourier transform (DFT) window start at the inter-symbol-interference (ISI)-free region. However, the multi-path uncertainty in wireless communication scenarios degrades the TS correctness. To alleviate this degradation, we propose a learning-based TS method enhanced by improving the design of training label. In the proposed method, the classic cross-correlator extracts the initial TS feature for benefiting the following machine learning. Wherein, the network architecture unfolds one classic cross-correlation process. Against the multi-path uncertainty, a novel training label is designed by representing the ISI-free region and especially highlighting its approximate midpoint. Therein, the closer to the region boundary of ISI-free the smaller label values are set, expecting to locate the maximum network output in ISI-free region with a high probability. Then, to guarantee the correctness of labeling, we exploit the priori information of line-of-sight (LOS) to form a LOS-aided labeling. Numerical results confirm that, the proposed training label effectively enhances the correctness of the proposed TS learner against the multi-path uncertainty.