diff --git a/compiler/src/dotty/tools/dotc/inlines/Inliner.scala b/compiler/src/dotty/tools/dotc/inlines/Inliner.scala
index 7c79e972c126..c1a1f7dbeb87 100644
--- a/compiler/src/dotty/tools/dotc/inlines/Inliner.scala
+++ b/compiler/src/dotty/tools/dotc/inlines/Inliner.scala
@@ -381,6 +381,13 @@ class Inliner(val call: tpd.Tree)(using Context):
   private val mapOpaques = TreeTypeMap(
       typeMap = new TypeMap:
           override def stopAt = StopAt.Package
+          override protected def derivedAppliedType(tp: AppliedType, tycon: Type, args: List[Type]): Type =
+            if (args ne tp.args) && tp.isMatchAlias && tp.tryNormalize.exists then
+              // #20427: A match type with mapped arguments might fail to reduce
+              // (narrowing doesn't hold for match types), so prefer reducing
+              // them if possible.
+              apply(tp.normalized)
+            else super.derivedAppliedType(tp, tycon, args)
           def apply(t: Type) = mapOver {
             t match
               case ref: TermRef => mapRef(ref).getOrElse(ref)
diff --git a/compiler/test/dotc/pos-test-pickling.blacklist b/compiler/test/dotc/pos-test-pickling.blacklist
index d6f962176ecc..f5db4565e801 100644
--- a/compiler/test/dotc/pos-test-pickling.blacklist
+++ b/compiler/test/dotc/pos-test-pickling.blacklist
@@ -67,6 +67,7 @@ mt-redux-norm.perspective.scala
 i18211.scala
 10867.scala
 named-tuples1.scala
+inline-match-opaque.scala
 
 # Opaque type
 i5720.scala
diff --git a/tests/pos/inline-match-opaque-2.scala b/tests/pos/inline-match-opaque-2.scala
new file mode 100644
index 000000000000..c0ea004a8a90
--- /dev/null
+++ b/tests/pos/inline-match-opaque-2.scala
@@ -0,0 +1,6 @@
+import scala.language.experimental.namedTuples
+
+object Test:
+  type NT = NamedTuple.Concat[(hi: Int), (bla: String)]
+  def foo(x: NT) =
+    x.hi // error
diff --git a/tests/pos/inline-match-opaque.scala b/tests/pos/inline-match-opaque.scala
new file mode 100644
index 000000000000..f4ed03542ff5
--- /dev/null
+++ b/tests/pos/inline-match-opaque.scala
@@ -0,0 +1,19 @@
+object Foo:
+  opaque type Wrapper[T] = T
+  def part[T](w: Wrapper[T]): T = w
+  inline def part2[T](w: Wrapper[T]): T = part(w) //part(w.asInstanceOf[Wrapper[T]]) also fixes the issue
+  type Rewrap[W] = Wrapper[Extra.Unwrap[W]]
+
+object Extra:
+  type Unwrap[W] = W match
+    case Foo.Wrapper[t] => t
+  type Rewrap[W] = Foo.Wrapper[Unwrap[W]]
+
+object Test:
+  type X = Extra.Rewrap[Foo.Wrapper[Int]]
+  def foo1(x: Foo.Wrapper[Extra.Unwrap[Foo.Wrapper[Int]]]) =
+    Foo.part(x) // ok
+    Foo.part2(x) // ok
+  def foo2(x: X) =
+    Foo.part(x) // ok
+    Foo.part2(x) // error