diff --git a/compiler/src/dotty/tools/dotc/core/TypeComparer.scala b/compiler/src/dotty/tools/dotc/core/TypeComparer.scala
index 7bb942e9ab6a..ac0305deac42 100644
--- a/compiler/src/dotty/tools/dotc/core/TypeComparer.scala
+++ b/compiler/src/dotty/tools/dotc/core/TypeComparer.scala
@@ -2404,7 +2404,8 @@ class TypeComparer(@constructorOnly initctx: Context) extends ConstraintHandling
    *  1. Single inheritance of classes
    *  2. Final classes cannot be extended
    *  3. ConstantTypes with distinct values are non intersecting
-   *  4. There is no value of type Nothing
+   *  4. TermRefs with distinct values are non intersecting
+   *  5. There is no value of type Nothing
    *
    *  Note on soundness: the correctness of match types relies on on the
    *  property that in all possible contexts, the same match type expression
@@ -2412,6 +2413,11 @@ class TypeComparer(@constructorOnly initctx: Context) extends ConstraintHandling
    */
   def provablyDisjoint(tp1: Type, tp2: Type)(using Context): Boolean = {
     // println(s"provablyDisjoint(${tp1.show}, ${tp2.show})")
+
+    def isEnumValueOrModule(ref: TermRef): Boolean =
+      val sym = ref.termSymbol
+      sym.isAllOf(EnumCase, butNot=JavaDefined) || sym.is(Module)
+
     /** Can we enumerate all instantiations of this type? */
     def isClosedSum(tp: Symbol): Boolean =
       tp.is(Sealed) && tp.isOneOf(AbstractOrTrait) && !tp.hasAnonymousChild
@@ -2517,6 +2523,8 @@ class TypeComparer(@constructorOnly initctx: Context) extends ConstraintHandling
         provablyDisjoint(gadtBounds(tp1.symbol).hi, tp2) || provablyDisjoint(tp1.superType, tp2)
       case (_, tp2: NamedType) if gadtBounds(tp2.symbol) != null =>
         provablyDisjoint(tp1, gadtBounds(tp2.symbol).hi) || provablyDisjoint(tp1, tp2.superType)
+      case (tp1: TermRef, tp2: TermRef) if isEnumValueOrModule(tp1) && isEnumValueOrModule(tp2) =>
+        tp1.termSymbol != tp2.termSymbol
       case (tp1: TypeProxy, tp2: TypeProxy) =>
         provablyDisjoint(matchTypeSuperType(tp1), tp2) || provablyDisjoint(tp1, matchTypeSuperType(tp2))
       case (tp1: TypeProxy, _) =>
diff --git a/compiler/test/dotc/pos-from-tasty.blacklist b/compiler/test/dotc/pos-from-tasty.blacklist
index 51fb4980f30c..b0ea2e35caec 100644
--- a/compiler/test/dotc/pos-from-tasty.blacklist
+++ b/compiler/test/dotc/pos-from-tasty.blacklist
@@ -8,3 +8,6 @@ t802.scala
 
 # missing position
 rbtree.scala
+
+# transitive reduction of match types
+i10511.scala
diff --git a/docs/docs/reference/new-types/match-types.md b/docs/docs/reference/new-types/match-types.md
index 72ee3f87384c..b849b9b7e237 100644
--- a/docs/docs/reference/new-types/match-types.md
+++ b/docs/docs/reference/new-types/match-types.md
@@ -48,7 +48,7 @@ Recursive match type definitions can also be given an upper bound, like this:
 
 ```scala
 type Concat[Xs <: Tuple, +Ys <: Tuple] <: Tuple = Xs match
-   case Unit => Ys
+   case EmptyTuple => Ys
    case x *: xs => x *: Concat[xs, Ys]
 ```
 
@@ -126,6 +126,7 @@ Disjointness proofs rely on the following properties of Scala types:
 1. Single inheritance of classes
 2. Final classes cannot be extended
 3. Constant types with distinct values are nonintersecting
+4. Singleton paths to distinct values are nonintersecting, such as `object` definitions or singleton enum cases.
 
 Type parameters in patterns are minimally instantiated when computing `S <: Pi`.
 An instantiation `Is` is _minimal_ for `Xs` if all type variables in `Xs` that
@@ -240,4 +241,3 @@ main differences here are:
    whereas match types also work for type parameters and abstract types.
  - Match types support direct recursion.
  - Conditional types distribute through union types.
-
diff --git a/tests/neg/i10511.scala b/tests/neg/i10511.scala
new file mode 100644
index 000000000000..4ceaae4141e4
--- /dev/null
+++ b/tests/neg/i10511.scala
@@ -0,0 +1,18 @@
+enum Bool {
+  case True
+  case False
+}
+
+import Bool._
+
+type Not[B <: Bool] = B match {
+  case True.type => False.type
+  case False.type => True.type
+}
+
+def not[B <: Bool & Singleton](b: B): Not[B] = b match {
+  case b: False.type => True // error
+  case b: True.type => False // error
+}
+
+val f: Not[False.type] = False // error: Found: (Bool.False : Bool) Required: (Bool.True : Bool)
diff --git a/tests/pos/i10511.scala b/tests/pos/i10511.scala
new file mode 100644
index 000000000000..386899d047a7
--- /dev/null
+++ b/tests/pos/i10511.scala
@@ -0,0 +1,22 @@
+enum Bool {
+  case True
+  case False
+}
+
+import Bool._
+
+type Not[B <: Bool] = B match {
+  case True.type => False.type
+  case False.type => True.type
+}
+
+val t: True.type = True
+val f: False.type = False
+
+val g: Not[False.type] = t
+
+val t1: Not[f.type] = t // transitivity
+val f1: Not[t.type] = f // transitivity
+
+val t2: Not[f1.type] = t1 // transitivity x2
+val f2: Not[t1.type] = f1 // transitivity x2
diff --git a/tests/run/i10511.scala b/tests/run/i10511.scala
new file mode 100644
index 000000000000..f1548ea7482a
--- /dev/null
+++ b/tests/run/i10511.scala
@@ -0,0 +1,31 @@
+enum Bool {
+  case True
+  case False
+
+  // just to make sure we are using reference equality
+  override def equals(a: Any) = false
+
+}
+
+import Bool._
+
+type Not[B <: Bool] = B match {
+  case True.type => False.type
+  case False.type => True.type
+}
+
+def not[B <: Bool & Singleton](b: B): Not[B] = b match {
+  case b: True.type => False
+  case b: False.type => True
+}
+
+@main def Test =
+
+  val t: True.type = True
+  val f: False.type = False
+
+  val t1: Not[False.type] = t
+  val f1: Not[True.type] = f
+
+  assert(not(True).asInstanceOf[AnyRef] eq False)
+  assert(not(False).asInstanceOf[AnyRef] eq True)