Boll distribution provides an important assessment of the response and adaptation of upland cotton (Gossypium hirsutum L.) to its environment and is strongly linked to yield and fiber quality and consequently to economic value. Several studies have measured boll distribution through end-of-season field or box mapping to study the spatiotemporal characteristics of bolls at both the plant and field levels, to quantify the effects of stress on cotton maturity and fiber quality, and to estimate yield as a function of the relative partitioning of resources to competing sinks. This paper discusses the environmental factors affecting boll production and distribution, reviews methods of measuring and analyzing boll distribution, and discusses the comparative advantages and drawbacks of these methods. With the advent of advanced imaging technologies, this paper also discusses the potential transition from traditional methods to machine-based boll distribution measurements, the challenges associated with these technologies, and how continuous improvements in the baseline technologies being used in the different methods will translate to improved measurement capacities. Overall, major strides can still be made in the area of boll distribution measurement by combining the positive elements in the different studies described in this review to circumvent each of their respective limitations.