diff --git a/compiler/src/dotty/tools/dotc/core/SymDenotations.scala b/compiler/src/dotty/tools/dotc/core/SymDenotations.scala
index 0342e8291495..1b5e63d0a2a0 100644
--- a/compiler/src/dotty/tools/dotc/core/SymDenotations.scala
+++ b/compiler/src/dotty/tools/dotc/core/SymDenotations.scala
@@ -1806,6 +1806,11 @@ object SymDenotations {
     def baseClasses(implicit onBehalf: BaseData, ctx: Context): List[ClassSymbol] =
       baseData._1
 
+    /** Like `baseClasses.length` but more efficient. */
+    def baseClassesLength(using BaseData, Context): Int =
+      // `+ 1` because the baseClassSet does not include the current class unlike baseClasses
+      baseClassSet.classIds.length + 1
+
     /** A bitset that contains the superId's of all base classes */
     private def baseClassSet(implicit onBehalf: BaseData, ctx: Context): BaseClassSet =
       baseData._2
diff --git a/compiler/src/dotty/tools/dotc/typer/Implicits.scala b/compiler/src/dotty/tools/dotc/typer/Implicits.scala
index 2b01a7245969..7b743aaab49f 100644
--- a/compiler/src/dotty/tools/dotc/typer/Implicits.scala
+++ b/compiler/src/dotty/tools/dotc/typer/Implicits.scala
@@ -1247,53 +1247,112 @@ trait Implicits:
              |Consider using the scala.util.NotGiven class to implement similar functionality.""",
              ctx.source.atSpan(span))
 
-      /** A relation that influences the order in which implicits are tried.
+      /** Compare the length of the baseClasses of two symbols (except for objects,
+       *  where we use the length of the companion class instead if it's bigger).
+       *
+       *  This relation is meant to approximate `Applications#compareOwner` while also
+       *  inducing a total ordering: `compareOwner` returns `0` for unrelated symbols
+       *  and therefore only induces a partial ordering, meaning it cannot be used
+       *  as a sorting function (see `java.util.Comparator#compare`).
+       */
+      def compareBaseClassesLength(sym1: Symbol, sym2: Symbol): Int =
+        def len(sym: Symbol) =
+          if sym.is(ModuleClass) && sym.companionClass.exists then
+            Math.max(sym.asClass.baseClassesLength, sym.companionClass.asClass.baseClassesLength)
+          else if sym.isClass then
+            sym.asClass.baseClassesLength
+          else
+            0
+        len(sym1) - len(sym2)
+
+      /** A relation that influences the order in which eligible implicits are tried.
+       *
        *  We prefer (in order of importance)
        *   1. more deeply nested definitions
        *   2. definitions with fewer implicit parameters
-       *   3. definitions in subclasses
+       *   3. definitions whose owner has more parents (see `compareBaseClassesLength`)
        *  The reason for (2) is that we want to fail fast if the search type
        *  is underconstrained. So we look for "small" goals first, because that
        *  will give an ambiguity quickly.
        */
-      def prefer(cand1: Candidate, cand2: Candidate): Boolean =
-        val level1 = cand1.level
-        val level2 = cand2.level
-        if level1 > level2 then return true
-        if level1 < level2 then return false
-        val sym1 = cand1.ref.symbol
-        val sym2 = cand2.ref.symbol
+      def compareEligibles(e1: Candidate, e2: Candidate): Int =
+        if e1 eq e2 then return 0
+        val cmpLevel = e1.level - e2.level
+        if cmpLevel != 0 then return -cmpLevel // 1.
+        val sym1 = e1.ref.symbol
+        val sym2 = e2.ref.symbol
         val arity1 = sym1.info.firstParamTypes.length
         val arity2 = sym2.info.firstParamTypes.length
-        if arity1 < arity2 then return true
-        if arity1 > arity2 then return false
-        compareOwner(sym1.owner, sym2.owner) == 1
+        val cmpArity = arity1 - arity2
+        if cmpArity != 0 then return cmpArity // 2.
+        val cmpBcs = compareBaseClassesLength(sym1.owner, sym2.owner)
+        -cmpBcs // 3.
 
-      /** Sort list of implicit references according to `prefer`.
+      /** Check if `ord` respects the contract of `Ordering`.
+       *
+       *  More precisely, we check that its `compare` method respects the invariants listed
+       *  in https://docs.oracle.com/javase/8/docs/api/java/util/Comparator.html#compare-T-T-
+       */
+      def validateOrdering(ord: Ordering[Candidate]): Unit =
+        for
+          x <- eligible
+          y <- eligible
+          cmpXY = Integer.signum(ord.compare(x, y))
+          cmpYX = Integer.signum(ord.compare(y, x))
+          z <- eligible
+          cmpXZ = Integer.signum(ord.compare(x, z))
+          cmpYZ = Integer.signum(ord.compare(y, z))
+        do
+          def reportViolation(msg: String): Unit =
+            Console.err.println(s"Internal error: comparison function violated ${msg.stripMargin}")
+          def showCandidate(c: Candidate): String =
+            s"$c (${c.ref.symbol.showLocated})"
+
+          if cmpXY != -cmpYX then
+            reportViolation(
+              s"""signum(cmp(x, y)) == -signum(cmp(y, x)) given:
+                 |x = ${showCandidate(x)}
+                 |y = ${showCandidate(y)}
+                 |cmpXY = $cmpXY
+                 |cmpYX = $cmpYX""")
+          if cmpXY != 0 && cmpXY == cmpYZ && cmpXZ != cmpXY then
+            reportViolation(
+              s"""transitivity given:
+                 |x = ${showCandidate(x)}
+                 |y = ${showCandidate(y)}
+                 |z = ${showCandidate(z)}
+                 |cmpXY = $cmpXY
+                 |cmpXZ = $cmpXZ
+                 |cmpYZ = $cmpYZ""")
+          if cmpXY == 0 && cmpXZ != cmpYZ then
+            reportViolation(
+              s"""cmp(x, y) == 0 implies that signum(cmp(x, z)) == signum(cmp(y, z)) given:
+                 |x = ${showCandidate(x)}
+                 |y = ${showCandidate(y)}
+                 |z = ${showCandidate(z)}
+                 |cmpXY = $cmpXY
+                 |cmpXZ = $cmpXZ
+                 |cmpYZ = $cmpYZ""")
+      end validateOrdering
+
+      /** Sort list of implicit references according to `compareEligibles`.
        *  This is just an optimization that aims at reducing the average
        *  number of candidates to be tested.
        */
-      def sort(eligible: List[Candidate]) = eligible match {
+      def sort(eligible: List[Candidate]) = eligible match
         case Nil => eligible
         case e1 :: Nil => eligible
         case e1 :: e2 :: Nil =>
-          if (prefer(e2, e1)) e2 :: e1 :: Nil
+          if compareEligibles(e2, e1) < 0 then e2 :: e1 :: Nil
           else eligible
         case _ =>
-          try eligible.sortWith(prefer)
+          val ord: Ordering[Candidate] = (a, b) => compareEligibles(a, b)
+          try eligible.sorted(using ord)
           catch case ex: IllegalArgumentException =>
-            // diagnostic to see what went wrong
-            for
-              e1 <- eligible
-              e2 <- eligible
-              if prefer(e1, e2)
-              e3 <- eligible
-              if prefer(e2, e3) && !prefer(e1, e3)
-            do
-              val es = List(e1, e2, e3)
-              println(i"transitivity violated for $es%, %\n ${es.map(_.implicitRef.underlyingRef.symbol.showLocated)}%, %")
+            // This exception being thrown probably means that our comparison
+            // function is broken, check if that's the case
+            validateOrdering(ord)
             throw ex
-      }
 
       rank(sort(eligible), NoMatchingImplicitsFailure, Nil)
     end searchImplicit