diff --git a/compiler/src/dotty/tools/dotc/inlines/Inliner.scala b/compiler/src/dotty/tools/dotc/inlines/Inliner.scala
index 1b4d985c7c4c..a9c9568d0d31 100644
--- a/compiler/src/dotty/tools/dotc/inlines/Inliner.scala
+++ b/compiler/src/dotty/tools/dotc/inlines/Inliner.scala
@@ -860,46 +860,71 @@ class Inliner(val call: tpd.Tree)(using Context):
           case _ => sel.tpe
         }
         val selType = if (sel.isEmpty) wideSelType else selTyped(sel)
-        reduceInlineMatch(sel, selType, cases.asInstanceOf[List[CaseDef]], this) match {
-          case Some((caseBindings, rhs0)) =>
-            // drop type ascriptions/casts hiding pattern-bound types (which are now aliases after reducing the match)
-            // note that any actually necessary casts will be reinserted by the typing pass below
-            val rhs1 = rhs0 match {
-              case Block(stats, t) if t.span.isSynthetic =>
-                t match {
-                  case Typed(expr, _) =>
-                    Block(stats, expr)
-                  case TypeApply(sel@Select(expr, _), _) if sel.symbol.isTypeCast =>
-                    Block(stats, expr)
-                  case _ =>
-                    rhs0
+
+        /** Make an Inlined that has no bindings. */
+        def flattenInlineBlock(tree: Tree): Tree = {
+          def inlineBlock(call: Tree, stats: List[Tree], expr: Tree): Block =
+            def inlinedTree(tree: Tree) = Inlined(call, Nil, tree).withSpan(tree.span)
+            val stats1 = stats.map:
+              case stat: ValDef => cpy.ValDef(stat)(rhs = inlinedTree(stat.rhs))
+              case stat: DefDef => cpy.DefDef(stat)(rhs = inlinedTree(stat.rhs))
+              case stat => inlinedTree(stat)
+            cpy.Block(tree)(stats1, flattenInlineBlock(inlinedTree(expr)))
+
+          tree match
+            case tree @ Inlined(call, bindings, expr) if !bindings.isEmpty =>
+              inlineBlock(call, bindings, expr)
+            case tree @ Inlined(call, Nil, Block(stats, expr)) =>
+              inlineBlock(call, stats, expr)
+            case _ =>
+              tree
+        }
+
+        def reduceInlineMatchExpr(sel: Tree): Tree = flattenInlineBlock(sel) match
+          case Block(stats, expr) =>
+            cpy.Block(sel)(stats, reduceInlineMatchExpr(expr))
+          case _ =>
+            reduceInlineMatch(sel, selType, cases.asInstanceOf[List[CaseDef]], this) match {
+              case Some((caseBindings, rhs0)) =>
+                // drop type ascriptions/casts hiding pattern-bound types (which are now aliases after reducing the match)
+                // note that any actually necessary casts will be reinserted by the typing pass below
+                val rhs1 = rhs0 match {
+                  case Block(stats, t) if t.span.isSynthetic =>
+                    t match {
+                      case Typed(expr, _) =>
+                        Block(stats, expr)
+                      case TypeApply(sel@Select(expr, _), _) if sel.symbol.isTypeCast =>
+                        Block(stats, expr)
+                      case _ =>
+                        rhs0
+                    }
+                  case _ => rhs0
                 }
-              case _ => rhs0
-            }
-            val rhs2 = rhs1 match {
-              case Typed(expr, tpt) if rhs1.span.isSynthetic => constToLiteral(expr)
-              case _ => constToLiteral(rhs1)
+                val rhs2 = rhs1 match {
+                  case Typed(expr, tpt) if rhs1.span.isSynthetic => constToLiteral(expr)
+                  case _ => constToLiteral(rhs1)
+                }
+                val (usedBindings, rhs3) = dropUnusedDefs(caseBindings, rhs2)
+                val rhs = seq(usedBindings, rhs3)
+                inlining.println(i"""--- reduce:
+                                    |$tree
+                                    |--- to:
+                                    |$rhs""")
+                typedExpr(rhs, pt)
+              case None =>
+                def guardStr(guard: untpd.Tree) = if (guard.isEmpty) "" else i" if $guard"
+                def patStr(cdef: untpd.CaseDef) = i"case ${cdef.pat}${guardStr(cdef.guard)}"
+                val msg =
+                  if (tree.selector.isEmpty)
+                    em"""cannot reduce summonFrom with
+                      | patterns :  ${tree.cases.map(patStr).mkString("\n             ")}"""
+                  else
+                    em"""cannot reduce inline match with
+                        | scrutinee:  $sel : ${selType}
+                        | patterns :  ${tree.cases.map(patStr).mkString("\n             ")}"""
+                errorTree(tree, msg)
             }
-            val (usedBindings, rhs3) = dropUnusedDefs(caseBindings, rhs2)
-            val rhs = seq(usedBindings, rhs3)
-            inlining.println(i"""--- reduce:
-                                |$tree
-                                |--- to:
-                                |$rhs""")
-            typedExpr(rhs, pt)
-          case None =>
-            def guardStr(guard: untpd.Tree) = if (guard.isEmpty) "" else i" if $guard"
-            def patStr(cdef: untpd.CaseDef) = i"case ${cdef.pat}${guardStr(cdef.guard)}"
-            val msg =
-              if (tree.selector.isEmpty)
-                em"""cannot reduce summonFrom with
-                   | patterns :  ${tree.cases.map(patStr).mkString("\n             ")}"""
-              else
-                em"""cannot reduce inline match with
-                    | scrutinee:  $sel : ${selType}
-                    | patterns :  ${tree.cases.map(patStr).mkString("\n             ")}"""
-            errorTree(tree, msg)
-        }
+        reduceInlineMatchExpr(sel)
       }
 
     override def newLikeThis(nestingLevel: Int): Typer = new InlineTyper(initialErrorCount, nestingLevel)
diff --git a/compiler/test/dotty/tools/backend/jvm/InlineBytecodeTests.scala b/compiler/test/dotty/tools/backend/jvm/InlineBytecodeTests.scala
index fcbc738f2934..b490d55bb43f 100644
--- a/compiler/test/dotty/tools/backend/jvm/InlineBytecodeTests.scala
+++ b/compiler/test/dotty/tools/backend/jvm/InlineBytecodeTests.scala
@@ -785,4 +785,36 @@ class InlineBytecodeTests extends DottyBytecodeTest {
     }
   }
 
+  @Test def inline_match_scrutinee_with_side_effect = {
+    val source = """class Test:
+                   |  inline def inlineTest(): Int =
+                   |    inline {
+                   |      println("scrutinee")
+                   |      (1, 2)
+                   |    } match
+                   |      case (e1, e2) => e1 + e2
+                   |
+                   |  def test: Int = inlineTest()
+                 """.stripMargin
+
+    checkBCode(source) { dir =>
+      val clsIn      = dir.lookupName("Test.class", directory = false).input
+      val clsNode    = loadClassNode(clsIn)
+
+      val fun = getMethod(clsNode, "test")
+      val instructions = instructionsFromMethod(fun)
+      val expected = List(
+        Field(GETSTATIC, "scala/Predef$", "MODULE$", "Lscala/Predef$;"),
+        Ldc(LDC, "scrutinee"),
+        Invoke(INVOKEVIRTUAL, "scala/Predef$", "println", "(Ljava/lang/Object;)V", false),
+        Op(ICONST_3),
+        Op(IRETURN),
+      )
+
+      assert(instructions == expected,
+        "`i was not properly inlined in `test`\n" + diffInstructions(instructions, expected))
+
+    }
+  }
+
 }
diff --git a/tests/pos/i18151a.scala b/tests/pos/i18151a.scala
new file mode 100644
index 000000000000..6be2c5c23a30
--- /dev/null
+++ b/tests/pos/i18151a.scala
@@ -0,0 +1,10 @@
+case class El[A](attr: String, child: String)
+
+transparent inline def inlineTest(): String =
+  inline {
+    val el: El[Any] = El("1", "2")
+    El[Any](el.attr, el.child)
+  } match
+    case El(attr, child) => attr + child
+
+def test: Unit = inlineTest()
diff --git a/tests/pos/i18151b.scala b/tests/pos/i18151b.scala
new file mode 100644
index 000000000000..01d2aaee972a
--- /dev/null
+++ b/tests/pos/i18151b.scala
@@ -0,0 +1,10 @@
+case class El[A](val attr: String, val child: String)
+
+transparent inline def tmplStr(inline t: El[Any]): String =
+  inline t match
+    case El(attr, child) => attr + child
+
+def test: Unit = tmplStr {
+  val el = El("1", "2")
+  El[Any](el.attr, null)
+}
diff --git a/tests/pos/i18151c.scala b/tests/pos/i18151c.scala
new file mode 100644
index 000000000000..a46ec9dd927c
--- /dev/null
+++ b/tests/pos/i18151c.scala
@@ -0,0 +1,39 @@
+import scala.compiletime.*
+import scala.compiletime.ops.any.ToString
+
+trait Attr
+case object EmptyAttr extends Attr
+transparent inline def attrStr(inline a: Attr): String = inline a match
+  case EmptyAttr => ""
+transparent inline def attrStrHelper(inline a: Attr): String = inline a match
+  case EmptyAttr => ""
+trait TmplNode
+case class El[T <: String & Singleton, A <: Attr, C <: Tmpl](val tag: T, val attr: A, val child: C)
+    extends TmplNode
+case class Sib[L <: Tmpl, R <: Tmpl](left: L, right: R) extends TmplNode
+type TmplSingleton = String | Char | Int | Long | Float | Double | Boolean
+type Tmpl = TmplNode | Unit | (TmplSingleton & Singleton)
+transparent inline def tmplStr(inline t: Tmpl): String = inline t match
+  case El(tag, attr, child) => inline attrStr(attr) match
+      case "" => "<" + tag + ">" + tmplStr(child)
+      case x  => "<" + tag + " " + x + ">" + tmplStr(child)
+  case Sib(left, right) => inline tmplStr(right) match
+      case ""    => tmplStr(left)
+      case right => tmplStrHelper(left) + right
+  case ()                     => ""
+  case s: (t & TmplSingleton) => constValue[ToString[t]]
+transparent inline def tmplStrHelper(inline t: Tmpl): String = inline t match
+  case El(tag, attr, child) => inline (tmplStr(child), attrStr(attr)) match
+      case ("", "")      => "<" + tag + "/>"
+      case (child, "")   => "<" + tag + ">" + child + "</" + tag + ">"
+      case ("", attr)    => "<" + tag + " " + attr + "/>"
+      case (child, attr) => "<" + tag + " " + attr + ">" + child + "</" + tag + ">"
+  case Sib(left, right)       => tmplStrHelper(left) + tmplStrHelper(right)
+  case ()                     => ""
+  case s: (t & TmplSingleton) => constValue[ToString[t]]
+transparent inline def el(tag: String & Singleton): El[tag.type, EmptyAttr.type, Unit] =
+  El(tag, EmptyAttr, ())
+extension [T <: String & Singleton, A <: Attr, C <: Tmpl](el: El[T, A, C])
+  transparent inline def >>[C2 <: Tmpl](child: C2) = El(el.tag, el.attr, el.child ++ child)
+
+extension [L <: Tmpl](left: L) transparent inline def ++[R <: Tmpl](right: R) = Sib(left, right)