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A general solution may be to define a specific comparison function that works on the structure you want. myOrder[a_, b_] := OrderedQ[{b[[1, 2]], a[[1, 2]]}] Sort[{{{1, l, 1}, 3}, {{3, q, 2}, 4}, {{2, a, 3}, 5}}, myOrder[#1, #2] &] ...