To investigate dissection severity, need for bailout stenting and limb outcomes in patients undergoing antegrade vs. retrograde revascularisation. Consecutive patients who underwent antegrade vs. retrograde revascularisation after antegrade recanalisation failure of long femoropopliteal chronic total occlusion (CTO) due to symptomatic peripheral artery disease between January 2017 and June 2022 were studied. Retrospective case-control matching was used to adjust for lesion length and calcification using the peripheral artery calcification scoring system (PACSS). Procedural outcomes included severity of dissection (Type A to F dissections, numerically graded on a scale from 0 - 6 with increasing severity) after angioplasty and number and localisation of stents needed to be implanted during the index procedure. Additionally, clinically driven target lesion revascularisation (CD-TLR) and major (above the ankle) amputation rates were assessed during follow up. A total of 180 patients were analysed who underwent antegrade (n = 90) vs. retrograde after failed antegrade (n = 90) recanalisation. Median patient age was 76.0 (interquartile range [IQR] 67.0, 82.0) years and 76 (42.2%) were female. Moreover, 78 patients (43.3%) had intermittent claudication, whereas 102 (56.7%) exhibited chronic limb threatening ischaemia (CLTI). Mean lesion length was 30.0 (IQR 24.0, 36.0) cm with moderate to severe (3.0 [IQR 2.0, 4.0]) lesion calcification. Dissection severity after angioplasty was higher in antegrade vs. retrograde after failed antegrade recanalisation (4.0 [IQR 3.0, 4.0] vs. 3.0 [IQR 2.0, 4.0]; p < .001). Additionally, the number of stents in all segments and the rate of bailout stenting in popliteal segments was significantly higher with the antegrade strategy (2.0 [IQR 1.0, 3.0] vs. 1.0 [IQR 0, 2.0], p < .010; and 37% vs. 14%, p < .001). During median follow up of 1.48 (IQR 0.63, 3.09) years, CD-TLR rates (p = .90) and amputation rates in patients with CLTI (p = .15) were not statistically significant. In complex femoropopliteal CTOs, retrograde after failed antegrade recanalisation is safe for endovascular revascularisation, which in experienced hands may result in less severe dissections and lower rates of stent placement. However, considering the relatively short follow up duration, CD-TLR and amputation rates were not statistically different between the two approaches. [German Clinical Trials Register: DRKS00015277.].