diff --git a/compiler/src/dotty/tools/dotc/typer/Implicits.scala b/compiler/src/dotty/tools/dotc/typer/Implicits.scala
index f0788665ca17..a9a75735c7e0 100644
--- a/compiler/src/dotty/tools/dotc/typer/Implicits.scala
+++ b/compiler/src/dotty/tools/dotc/typer/Implicits.scala
@@ -60,6 +60,7 @@ object Implicits {
 
     /** Return those references in `refs` that are compatible with type `pt`. */
     protected def filterMatching(pt: Type)(implicit ctx: Context): List[Candidate] = track("filterMatching") {
+      val ptNorm = normalize(pt, pt) // `pt` could be implicit function types, check i2749
 
       def refMatches(ref: TermRef)(implicit ctx: Context) = /*ctx.traceIndented(i"refMatches $ref $pt")*/ {
 
@@ -123,7 +124,8 @@ object Implicits {
             record("discarded eligible")
             false
           }
-          else NoViewsAllowed.isCompatible(normalize(ref, pt), pt)
+          else
+            NoViewsAllowed.isCompatible(normalize(ref, pt), ptNorm)
         }
       }
 
diff --git a/compiler/src/dotty/tools/dotc/typer/Typer.scala b/compiler/src/dotty/tools/dotc/typer/Typer.scala
index 974c9786799a..632acca1f00d 100644
--- a/compiler/src/dotty/tools/dotc/typer/Typer.scala
+++ b/compiler/src/dotty/tools/dotc/typer/Typer.scala
@@ -1640,6 +1640,7 @@ class Typer extends Namer with TypeAssigner with Applications with Implicits wit
         if (defn.isImplicitFunctionType(pt) &&
             xtree.isTerm &&
             !untpd.isImplicitClosure(xtree) &&
+            !ctx.mode.is(Mode.ImplicitShadowing) &&
             !ctx.isAfterTyper)
           makeImplicitFunction(xtree, pt)
         else xtree match {
diff --git a/tests/pos/i2749.scala b/tests/pos/i2749.scala
new file mode 100644
index 000000000000..5d4972421ebb
--- /dev/null
+++ b/tests/pos/i2749.scala
@@ -0,0 +1,23 @@
+object Test {
+  val f: implicit (implicit Int => Char) => Boolean = ???
+  implicit val n: Int = 3
+  implicit val g: implicit Int => Char = ???
+
+  f : Boolean
+}
+
+object Test2 {
+  val f: implicit (implicit Int => Char) => Boolean = ???
+  implicit val s: String = null
+  implicit val g: implicit Int => implicit String => Char = ???
+
+  f : Boolean
+}
+
+object Test3 {
+  val f: implicit (implicit Int => implicit String => Char) => Boolean = ???
+  implicit val n: Int = 3
+  implicit val g: implicit Int => Char = ???
+
+  f : Boolean
+}