We enumerate rational curves in toric surfaces passing through points and satisfying cross-ratio constraints using tropical and combinatorial methods. Our starting point is arXiv:1509.07453, where a tropical-algebraic correspondence theorem was proved that relates counts of rational curves in toric varieties that satisfy point conditions and cross-ratio constraints to the analogous tropical counts. We proceed in two steps: based on tropical intersection theory we first study tropical cross-ratios and introduce degenerated cross-ratios. Second we provide a lattice path algorithm that produces all tropical curves satisfying such degenerated conditions explicitly. In a special case simpler combinatorial objects, so-called cross-ratio floor diagrams, are introduced which can be used to determine these enumerative numbers as well.