Precise detection of leaf nitrogen concentration (LNC) is helpful for nutrient diagnosis and fertilization guidance in farm crops. Numerous researchers have estimated LNC with techniques based on reflectance spectra or active chlorophyll fluorescence, which have limitations of low accuracy or small scale in the field. Given the correlation between chlorophyll and nitrogen contents, the response of sun-induced chlorophyll fluorescence (SIF) to chlorophyll (Chl) content reported in a few papers suggests the feasibility of quantifying LNC using SIF. Few studies have investigated the difference and power of the upward and downward SIF components on monitoring LNC in winter wheat. We conducted two field experiments to evaluate the capacity of SIF to monitor the LNC of winter wheat during the entire growth season and compare the differences of the upward and downward SIF for LNC detection. A FluoWat leaf clip coupled with a ASD spectrometer was used to measure the upward and downward SIF under sunlight. It was found that three (↓FY687, ↑FY687/↑FY739, and ↓FY687/↓FY739) out of the six SIF yield (FY) indices examined were significantly correlated to the LNC (R2 = 0.6, 0.51, 0.75, respectively). The downward SIF yield indices exhibited better performance than the upward FY indices in monitoring the LNC with the ↓FY687/↓FY739 being the best FY index. Moreover, the LNC models based on the three SIF yield indices are insensitive to the chlorophyll content and the leaf mass per area (LMA). These findings suggest the downward SIF should not be neglected for monitoring crop LNC at the leaf scale, although it is more difficult to measure with current instruments. The downward SIF could play an increasingly important role in understanding of the SIF emission for LNC detection at different scales. These results could provide a solid foundation for elucidating the mechanism of SIF for LNC estimation at the canopy scale.