Purpose To examine the frequency of computed tomography (CT)-guided biopsy sampling errors in chondrosarcomas, as well as the impact of these errors and the achieved surgical margins on local recurrence-free survival (LRFS) and disease-specific survival (DSS). Material and methods A total of 68 consecutive patients treated for chondrosarcoma from 2000-2015 were retrospectively reviewed with a minimum follow-up duration of 2 years. Results The primary location was at the extremities in 46 patients (67.6%) and at the axial skeleton in 22 patients (32.4%). Seven patients underwent planned intralesional curettage. Surgical margins were assessed in the remaining 53 patients and included 21 wide (39.6%), 25 marginal (47.1%), and seven intralesional (13.2%) resections. Biopsy sampling errors occurred in ten patients (14.7%). LRFS was 82.2±7.8% at 5 years and 76.9±7.8% at 10 years. An intact anatomical barrier was associated with the most preferable LRFS of 89±10.5% after 10 years. DSS was 79.2±8.5% at 5 years and 75.5±6.4% at 10 years. The metric distance of the surgical margin and the presence of a biopsy sampling error did not affect either LRFS or DSS. Conclusion Even though histological grading in chondrosarcoma is difficult, sampling errors in preoperative biopsies are relatively rare and do not adversely affect outcomes. The presence of an anatomical barrier has a greater impact on LRFS than the metric distance of the surgical margins.