The serpentine delay line (SDL) is commonly used as one kind of typical true time delay lines (TDLs) with periodic strong reflection points (SRPs). However, the Hilbert fractal curve delay lines (HFCDLs), with the same circuit area and the same spacing between the adjacent segment lines, are proven to have quite different SRPs with improved performance. An analytic analysis model is used to investigate the SRPs of the two-order and three-order HFCDLs, respectively, in which the structure symmetry is fully considered to make the relevant adjacent structure equivalent to a pair of parallel dual lines. Thus, the accumulated far-end crosstalk (FEXT) is derived in the HFCDLs, and the implicit periodic SRPs are revealed. Furthermore, the iterated two-order and three-order HFCDLs are investigated to validate the analysis model. Subsequently, the periodically loaded transmission line (PLTL) with and without strategic discontinuous structured guard lines (DSGLs) is, respectively, utilized in the three-order and two-order HFCDLs, and thus, the proposed structures possess better wideband cancelation of the FEXT accordingly. In the ultrawideband (UWB) range of dc–51 GHz, the typical return loss (RL) is less than 20 dB for the proposed two-order HFCDL and less than 15 dB for the proposed three-order HFCDL. Meanwhile, the fluctuations are eliminated in the group delay (GD) for the proposed two-order HFCDL. For the proposed three-order HFCDL, the delay fluctuations are observed at the high end of the UWB due to the enhanced near-end crosstalk (NEXT), while the delay fluctuations less than 72.2 ps are still obtained in the range of dc–35 GHz.