Hybrid poplars have demonstrated high productivity as short rotation woody crops (SRWC) in the Midwest USA, and the hybrid aspen “Crandon” (Populus alba L. × P. grandidenta Michx.) has exhibited particularly promising yields on marginal lands. However, a key obstacle for wider deployment is the lack of economic returns early in the rotation. Alleycropping has the potential to address this issue, especially when paired with crops such as winter triticale which complete their growth cycle early in the summer and therefore are expected to exert minimal competition on establishing trees. In addition, well-placed fertilizer in low rates at planting has the potential to improve tree establishment and shorten the rotation, which is also economically desirable. To test the potential productivity of “Crandon” alleycropped with winter triticale, plots were established on five topographic positions with four different rates of fertilizer placed in the planting hole. Trees were then harvested from the plots after each of the first three growing seasons. Fertilization resulted in significant increases in branch, stem, and total aboveground biomass across all years, whereas the effects of topographic position varied by year. Allocation between branches and stems was found to be primarily a function of total aboveground biomass.