Understanding how cherry tomatoes respond to variations in greenhouse microclimate is crucial for optimizing tomato production in a controlled environment. The present study delves into the intricate relationship between summer-grown cherry tomatoes (Cheramy F1) and greenhouse conditions, exploring the influence of these conditions on growth attributes, inflorescence development, and yield potential. The aim of the study was to characterize the chronology of reproductive events, specifically flowering and fruit stages, in correlation with the prevailing greenhouse climate during the development of the first ten inflorescences on the plant. The performance of each inflorescence has been ranked based on available data, which involve a comparative analysis of both the time duration (number of days) and the frequency of yield-contributing traits, specifically the total number of flowers at the anthesis stage. The duration of each stage required for completion was recorded and presented as a productivity rate factor. Greenhouse conditions exhibited variations during the vegetative and reproductive stages, respectively, as follows: temperature—25.1 °C and 21.33 °C, CO2 levels—484.85 ppm and 458.85 ppm, light intensity—367.94 W/m2 and 349.52 W/m2, and humidity—73.23% and 89.73%. The collected data conclusively demonstrated a substantial impact of greenhouse microclimate on plant growth, productivity, and inflorescence development. The development of flowers and fruit has been categorized into five stages: the fruit bud stage (FB), the anthesis stage (AS), the fruit setting stage (FS), the fruit maturation stage (FM), and the fruit ripening stage (FR). An irregular productivity and development response was noted across the first (close to roots) to the tenth inflorescence. Inflorescence 5 demonstrated the highest overall performance, followed by inflorescence numbers 4 and 6. The study findings provide valuable insights for enhancing greenhouse operations, emphasizing the improvement of both the yield and growth of cherry tomatoes while promoting environmental sustainability. A statistical analysis of variance was used to rigorously examine the presented results, conducted at a confidence level of p < 0.05.