diff --git a/compiler/src/dotty/tools/dotc/core/TypeComparer.scala b/compiler/src/dotty/tools/dotc/core/TypeComparer.scala
index 91f5c2258ea7..32d254f936bf 100644
--- a/compiler/src/dotty/tools/dotc/core/TypeComparer.scala
+++ b/compiler/src/dotty/tools/dotc/core/TypeComparer.scala
@@ -1257,7 +1257,7 @@ class TypeComparer(@constructorOnly initctx: Context) extends ConstraintHandling
       val savedSuccessCount = successCount
       try
         recCount += 1
-        if recCount >= Config.LogPendingSubTypesThreshold then monitored = true
+        if recCount >= Config.LogPendingSubTypesThreshold && !ctx.settings.YnoDeepSubtypes.value then monitored = true
         val result = if monitored then monitoredIsSubType else firstTry
         recCount -= 1
         if !result then
diff --git a/compiler/src/dotty/tools/dotc/core/Types.scala b/compiler/src/dotty/tools/dotc/core/Types.scala
index 44152c072468..3fc8e123da95 100644
--- a/compiler/src/dotty/tools/dotc/core/Types.scala
+++ b/compiler/src/dotty/tools/dotc/core/Types.scala
@@ -4490,7 +4490,7 @@ object Types {
         myReduced =
           trace(i"reduce match type $this $hashCode", typr, show = true) {
             def matchCases(cmp: TrackingTypeComparer): Type =
-              try cmp.matchCases(scrutinee.normalized, cases)
+              try cmp.matchCases(scrutinee.dealias.normalized, cases)
               catch case ex: Throwable =>
                 handleRecursive("reduce type ", i"$scrutinee match ...", ex)
               finally updateReductionContext(cmp.footprint)
diff --git a/compiler/test/dotc/pos-test-pickling.blacklist b/compiler/test/dotc/pos-test-pickling.blacklist
index 547a48d99b79..a6937f22087e 100644
--- a/compiler/test/dotc/pos-test-pickling.blacklist
+++ b/compiler/test/dotc/pos-test-pickling.blacklist
@@ -34,6 +34,7 @@ i7872.scala
 6687.scala
 i11236.scala
 i11247.scala
+9890.scala
 
 # Opaque type
 i5720.scala
diff --git a/tests/pos/9890.scala b/tests/pos/9890.scala
new file mode 100644
index 000000000000..96d6f1db33b7
--- /dev/null
+++ b/tests/pos/9890.scala
@@ -0,0 +1,49 @@
+object Test {
+  import scala.compiletime.ops.int._
+
+  trait x
+
+  type Range[Min <: Int, Max <: Int] <: Tuple = Min match {
+    case Max => EmptyTuple
+    case _ => Min *: Range[Min + 1, Max]
+  }
+
+  type TupleMap[Tup <: Tuple, Bound, F[_ <: Bound]] <: Tuple = Tup match {
+    case EmptyTuple => EmptyTuple
+    case h *: t => F[h] *: TupleMap[t, Bound, F]
+  }
+  type TupleDedup[Tup <: Tuple, Mask] <: Tuple = Tup match {
+    case EmptyTuple => EmptyTuple
+    case h *: t => h match {
+      case Mask => TupleDedup[t, Mask]
+      case _ => h *: TupleDedup[t, h | Mask]
+    }
+  }
+
+  type CoordToPos[r <: Int, c <: Int] = r * 9 + c
+  type Cell[r <: Int, c <: Int, Board <: Tuple] = Tuple.Elem[Board, CoordToPos[r, c]]
+  type Col[c <: Int, Board <: Tuple] = TupleMap[Range[0, 9], Int, [r <: Int] =>> Cell[r, c, Board]]
+
+  type ColFromPos[Pos <: Int] = Pos % 9
+
+  type Sudoku1 = (
+    x, x, x,  x, 1, x,  4, x, 6,
+    8, x, 1,  6, 2, x,  x, x, 9,
+    x, 3, x,  x, x, 9,  x, 2, x,
+
+    5, x, 9,  1, 3, x,  x, 6, x,
+    x, 6, x,  9, x, 2,  x, 4, x,
+    x, 2, x,  x, 6, 7,  8, x, 5,
+
+    x, 9, x,  5, x, x,  x, 3, x,
+    3, x, x,  x, 4, 6,  9, x, 7,
+    6, x, 7,  x, 9, x,  x, x, x,
+  )
+
+  //compiles fine
+  summon[Col[ColFromPos[0], Sudoku1] =:= (x, 8, x,  5, x, x,  x, 3, 6)]
+
+  summon[TupleDedup[(x, 8, x,  5, x, x,  x, 3, 6), Nothing] =:= (x, 8, 5, 3, 6)]
+  //but this doesn't
+  summon[TupleDedup[Col[ColFromPos[0], Sudoku1], Nothing] =:= (x, 8, 5, 3, 6)]
+}