The purpose of this study was to obtain a better understanding of probing measurements around osseointegrated oral implants. A comparison was made of probe tip position around Astra Tech implants and teeth of eight cynomolgus monkeys (Macaca fascicularis) in conditions of i) healthy peri-implant mucosa/gingiva, ii) mild mucositis/gingivitis, iii) severe mucositis/gingivitis or iv) peri-implantitis/periodontitis. Histological sections of 128 probes that were attached to implants or teeth with surrounding tissues were prepared by the cutting-grinding technique. No systematic differences were identified in the clinical and histological estimates of the distance between the mucosal/gingival margin and the probe tip. The differences were mainly smaller than 0.5 mm, and in no case were they larger than 0.7 mm. For implants and teeth with healthy peri-implant mucosa/gingiva, the distance between the probe tip and the alveolar bone was similar and ranged from 0.5 to 1.5 mm (P = 0.97). However, the probe tip was closer to bone around implants than around teeth in conditions of mild mucositis/gingivitis (P = 0.034), severe mucositis/gingivitis (P ≤ 0.0001) and peri-implantitis/periodontitis (Ps ≤ 0.0001). Around implants with severe mucositis and peri-implantitis, the distance was generally smaller than 0.5 mm, whereas teeth with severe gingivitis and periodontitis showed distances that mainly ranged from 0.5 to 1.5 mm. In conclusion, the probing measurements around osseointegrated oral implants and teeth were different. Even mild marginal inflammation was associated with deeper probe penetration around implants in comparison to teeth.