Two-dimensional chirality transfer from self-assembled (SA) molecules to covalently bonded products was achieved via on-surface synthesis on Au(111) substrates by choosing 1,4-dibromo-2,5-didodecylbenzene (12DB) and 1,4-dibromo-2,5-ditridecylbenzene (13DB) as designed precursors. Scanning tunneling microscopy investigations reveal that their aryl-aryl coupling reaction occurs by connecting the nearest neighboring precursors and thus preserving the SA lamellar structure. The SA structures of 12(13)DB precursors determine the final structures of produced oligo-p-phenylenes (OPP) on the surface. Pure homochiral domains (12DB) give rise to homochiral domains of OPP, whereas lamellae containing mixed chiral geometry of the precursor (13DB) results in the formation of racemic lamellae of OPP.