Cost-effective techniques for systematic archaeological prospection are essential to improve the efficiency of preventive archaeology and the preservation of cultural heritage. Web Mapping Services, such as Microsoft Bing Maps, provide imagery covering extensive areas at high resolution. These can, in some cases, reveal cropmarks of buried historical structures. Given that archaeological prospection is not generally the priority of most common Web Mapping Services, the conditions under which images are acquired are not always suitable for the appearance of cropmarks. Therefore, their detection is typically serendipitous. This pilot project attempts to assess the potential to use the Microsoft Bing Maps Bird’s Eye service within a crowdsourcing platform to systematically search for archaeological cropmarks in the surroundings of the city of Rome in Italy. On this platform, which is hosted by the company Scifabric (Southampton, UK) and based on PyBossa, an Open Source framework for crowdsourcing, members of the public are invited to interpret oblique air photo tiles of Bing Maps Bird’s Eye. While the project is still on-going, at least one seamless coverage of tiles in the area of interest has been interpreted. For each tile, the Bing Maps Bird’s Eye service provides oblique air photo coverage in up to four possible orientations. As of 5 July 2020, 18,765 of the total 67,014 tasks have been completed. Amongst these completed tasks, positive detections of cropmarks were recorded once for 1447 tasks, twice for 57 tasks, and three or more times for 10 tasks. While many of these detections may be erroneous, some correspond with archaeological cropmarks of buried remains of buildings, roads, aqueducts, and urban areas from the Roman period, as verified by comparison with archaeological survey data. This leads to the conclusion that the Bing Maps Bird’s Eye service contains a wealth of information useful for archaeological prospection, and that to a certain extent citizen researchers could help to mine this information. However, a more thorough analysis would need to be carried out on possible false negatives and biases related to the varying ease of interpretation of residues of different archaeological structures from multiple historical periods. This activity forms the first part of a research project on the systematic prospection of archaeological cropmarks. The ultimate aim is to reach a critical mass of training data through crowdsourcing which can be augmented and used as input to train a machine learning algorithm for automatic detection on a larger scale.