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<i>Toddalia asiatica</i> (L.) Lam. (Rutaceae) has shown a broad spectrum of biological properties, such as anti-inflammatory, antioxidant, antimicrobial, anti-HIV, and anticancer properties. The present study is concerned with the separation of the main components with broad partition coefficients (<i>K</i>_D values) from <i>T. asiatica</i>, using linear gradient high-speed counter-current chromatography (LGCCC) combined with an off-line two-dimensional (2D) mode. Similar to the binary gradient HPLC, the LGCCC mode is operated by the adjustment of the proportion between the mobile phase of 5:5:1:9 (<i>v</i>/<i>v</i>) (pump A) and 5:5:4.5:5.5 (<i>v</i>/<i>v</i>) (pump B) in an <i>n</i>-hexane/ethyl acetate/methanol/water solvent system. The off-line 2D-CCC mode was used in this study for the secondary separation of two similar <i>K</i>_D value compounds with <i>n</i>-hexane/ethyl acetate/methanol/water (5:5:4:6, <i>v</i>/<i>v</i>). Notably, six coumarins, namely, tomentin (<b>1</b>), toddalolactone (<b>2</b>), 5,7,8-trimethoxycoumarin (<b>3</b>), mexoticin (<b>4</b>), isopimpinellin (<b>5</b>), and toddanone (<b>6</b>), were efficiently separated. The structures of the pure compounds were elucidated by spectral techniques and compared with the literature.