Our society collects data on people for a wide range of applications, from building a census for policy evaluation to running meaningful clinical trials. To collect data, we typically sample individuals with the goal of accurately representing a population of interest. However, current sampling processes often collect data opportunistically from data sources, which can lead to datasets that are biased and not representative, i.e., the collected dataset does not accurately reflect the distribution of demographics of the true population. This is a concern because subgroups within the population can be under- or over-represented in a dataset, which may harm generalizability and lead to an unequal distribution of benefits and harms from downstream tasks that use such datasets (e.g., algorithmic bias in medical decision-making algorithms). In this paper, we assess the relationship between dataset representativeness and group-fairness of classifiers trained on that dataset. We demonstrate that there is a natural tension between dataset representativeness and classifier fairness; empirically we observe that training datasets with better representativeness can frequently result in classifiers with higher rates of unfairness. We provide some intuition as to why this occurs via a set of theoretical results in the case of univariate classifiers. We also find that over-sampling underrepresented groups can result in classifiers which exhibit greater bias to those groups. Lastly, we observe that fairness-aware sampling strategies (i.e., those which are specifically designed to select data with high downstream fairness) will often over-sample members of majority groups. These results demonstrate that the relationship between dataset representativeness and downstream classifier fairness is complex; balancing these two quantities requires special care from both model- and dataset-designers.