The phenanthrene skeleton is an important moiety in medical chemistry as it is present in steroidal drugs used as anti-inflammatory and anti-asthmatic agents as well as synthetic hormones or potassium sparing diuretics. Chromatographic properties of 14 derivatives containing the phenanthrene skeleton in their structure with known lipophilicity have been studied. NP, RP, and cyano-bonded silica stationary phases with three binary mobile phases (acetonitrile-water, acetone-water, and acetone-petroleum ether) were tested. Obtained chromatographic data were correlated with the lipophilicity expressed as values of log partition coefficient (P). The presented study was undertaken to find the best TLC system and chromatographic data processing method in order to predict log P values. Correlations between chromatographic data and measurements of lipophilicity of compounds were presented as results of established quantitative structure-retention relationships. Principal component analysis and cluster analysis were used to investigate the similarities among chromatographic systems.