[Object] A phosphorus-containing oligomer that has high solubility in an organic solvent and exhibits high flame retardancy and heat resistance in the form of a cured product thereof is provided. The phosphorus-containing oligomer is represented by structural formula (1) below(in the formula, R1 represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a phenyl group; n is the number of repeating units and an integer of 1 or more; X is a structural unit represented by structural formula (x1) or (x2) below;Y is a hydrogen atom, a hydroxyl group, or a structural unit represented by the structural formula (x1) or (x2); and, in the structural formula (x1) or (x2), R2, R3, R4, and R5 each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a phenyl group, or an aralkyl group), wherein the content of components whose n is 2 or more in the structural formula (1) is in the range of 5% to 90% in terms of peak area in GPC measurement.