In the east of China, low temperature and light energy in winter are the main factors for the decline in cucumber yield, as well as in greenhouses without supplementary light. Optimal utilization of light energy is critical to increase cucumber yield. In this study, experimental measurements were conducted in two scenarios, April to May (Apr-May) and November to December (Nov-Dec) 2015, respectively, to analyze leaf development, dry matter accumulation, and yield of cultivated cucumber. Statistical analysis showed that leaves grew in Nov-Dec had larger leaf area and lower dry matter than leaves grew in Apr-May. This revealed that the dry matter accumulation rate per unit area was lower in winter. To be precise, the yield 0.174 kg/m2 per day in Nov-Dec was 35.3% lower than the yield in Apr-May. Environmental monitoring data showed that there was no significant difference in the average temperature between two scenarios, but the light intensity in Nov-Dec was only 2/3 of that in Apr-May. Three-dimensional (3D) cucumber canopy models were used in this study to quantify the effects of weak light on dry matter production in Nov-Dec. Three 3D canopies of cucumber were reconstructed with 20, 25, and 30 leaves per plant, respectively, by using a parametric modeling method. Light interception of three canopies from 8:00 to 15:00 on 4 November 2015 was simulated by using the radiosity-graphic combined model (RGM) with an hourly time step. CO2 assimilation per unit area was calculated using the FvCB photosynthetic model. As a result, the effects of light intensity and CO2 concentration on the photosynthetic rate were considered. The leaf photosynthesis simulation result showed that during the daytime in winter, the RuBP regeneration-limited assimilation Aj was always less than the Rubisco-limited assimilation Ac. This means that the limiting factor affecting the photosynthesis rate in winter was rather light intensity. As the CO2 concentration in the greenhouse was utmost in the morning, increasing the light intensity and therefrom increasing the canopy light interception at this time will be highly beneficial to increase the yield production. Through a comparative analysis of photosynthetic characteristics in these three virtual 3D canopies, the 25-leaf canopy was the best-performed canopy structure in photosynthetic production in winter. This study provides an insight into the light deficiency for yield production in winter and a solution to make optimal use of light in the greenhouse.