diff --git a/compiler/src/dotty/tools/dotc/core/TypeComparer.scala b/compiler/src/dotty/tools/dotc/core/TypeComparer.scala
index 2ee4b6c6da5b..acb545efdca4 100644
--- a/compiler/src/dotty/tools/dotc/core/TypeComparer.scala
+++ b/compiler/src/dotty/tools/dotc/core/TypeComparer.scala
@@ -341,7 +341,7 @@ class TypeComparer(initctx: Context) extends ConstraintHandling[AbsentContext] w
         compareErasedValueType
       case ConstantType(v2) =>
         tp1 match {
-          case ConstantType(v1) => v1.value == v2.value
+          case ConstantType(v1) => v1.value == v2.value && recur(v1.tpe, v2.tpe)
           case _ => secondTry
         }
       case tp2: AnyConstantType =>
diff --git a/compiler/src/dotty/tools/dotc/typer/Applications.scala b/compiler/src/dotty/tools/dotc/typer/Applications.scala
index bf6b3d9a4600..44cd5b47c420 100644
--- a/compiler/src/dotty/tools/dotc/typer/Applications.scala
+++ b/compiler/src/dotty/tools/dotc/typer/Applications.scala
@@ -1948,7 +1948,7 @@ trait Applications extends Compatibility {
   }
 
   /** If `trees` all have numeric value types, and they do not have all the same type,
-   *  pick a common numeric supertype and convert all constant trees to this type.
+   *  pick a common numeric supertype and try to convert all constant Int literals to this type.
    *  If the resulting trees all have the same type, return them instead of the original ones.
    */
   def harmonize(trees: List[Tree])(implicit ctx: Context): List[Tree] = {
diff --git a/tests/pos/i5309.scala b/tests/pos/i5309.scala
new file mode 100644
index 000000000000..1aa653e736fb
--- /dev/null
+++ b/tests/pos/i5309.scala
@@ -0,0 +1,10 @@
+object A {
+  def foo[T](x: T, y: T): Int = 55
+  def bar[T](x: T, y: T): List[T] = x :: y :: Nil
+  val x = foo(23, 23f)
+  val y = bar(23, 23f)
+  val z = List(23, 23f)
+  val x2 = foo(23.0, 23)
+  val y2 = bar(23.0, 23)
+  val z2 = List(23.0, 23)
+}
\ No newline at end of file