diff --git a/src/msw/dir.cpp b/src/msw/dir.cpp
index 5b05d23d48..f406a91281 100644
--- a/src/msw/dir.cpp
+++ b/src/msw/dir.cpp
@@ -27,8 +27,11 @@
 
 #include "wx/dir.h"
 
-#ifdef __WINDOWS__
-    #include "wx/msw/private.h"
+#include "wx/msw/private.h"
+#include <shlwapi.h>
+
+#ifdef __VISUALC__
+    #pragma comment(lib, "shlwapi")
 #endif
 
 // ----------------------------------------------------------------------------
@@ -60,11 +63,6 @@ inline void FreeFindData(FIND_DATA fd)
     }
 }
 
-const wxChar *GetNameFromFindData(const FIND_STRUCT *finddata)
-{
-    return finddata->cFileName;
-}
-
 // Helper function checking that the contents of the given FIND_STRUCT really
 // match our filter. We need to do it ourselves as native Windows functions
 // apply the filter to both the long and the short names of the file, so
@@ -78,17 +76,7 @@ CheckFoundMatch(const FIND_STRUCT* finddata, const wxString& filter)
     if ( filter.empty() )
         return true;
 
-    // Otherwise do check the match validity. Notice that we must do it
-    // case-insensitively because the case of the file names is not supposed to
-    // matter under Windows.
-    wxString fn(GetNameFromFindData(finddata));
-
-    // However if the filter contains only special characters (which is a
-    // common case), we can skip the case conversion.
-    if ( filter.find_first_not_of(wxS("*?.")) == wxString::npos )
-        return fn.Matches(filter);
-
-    return fn.MakeUpper().Matches(filter.Upper());
+    return ::PathMatchSpec(finddata->cFileName, filter) == TRUE;
 }
 
 inline bool
@@ -130,11 +118,6 @@ FindFirst(const wxString& spec,
     return fd;
 }
 
-inline FIND_ATTR GetAttrFromFindData(FIND_STRUCT *finddata)
-{
-    return finddata->dwFileAttributes;
-}
-
 inline bool IsDir(FIND_ATTR attr)
 {
     return (attr & FILE_ATTRIBUTE_DIRECTORY) != 0;
@@ -231,7 +214,6 @@ bool wxDirData::Read(wxString *filename)
     bool first = false;
 
     WIN32_FIND_DATA finddata;
-    #define PTR_TO_FINDDATA (&finddata)
 
     if ( !IsFindDataOk(m_finddata) )
     {
@@ -246,7 +228,7 @@ bool wxDirData::Read(wxString *filename)
         else
             filespec += m_filespec;
 
-        m_finddata = FindFirst(filespec, m_filespec, PTR_TO_FINDDATA);
+        m_finddata = FindFirst(filespec, m_filespec, &finddata);
 
         first = true;
     }
@@ -265,9 +247,6 @@ bool wxDirData::Read(wxString *filename)
         return false;
     }
 
-    const wxChar *name;
-    FIND_ATTR attr;
-
     for ( ;; )
     {
         if ( first )
@@ -276,7 +255,7 @@ bool wxDirData::Read(wxString *filename)
         }
         else
         {
-            if ( !FindNext(m_finddata, m_filespec, PTR_TO_FINDDATA) )
+            if ( !FindNext(m_finddata, m_filespec, &finddata) )
             {
                 DWORD err = ::GetLastError();
 
@@ -290,8 +269,8 @@ bool wxDirData::Read(wxString *filename)
             }
         }
 
-        name = GetNameFromFindData(PTR_TO_FINDDATA);
-        attr = GetAttrFromFindData(PTR_TO_FINDDATA);
+        const wxChar* const name = finddata.cFileName;
+        const FIND_ATTR attr = finddata.dwFileAttributes;
 
         // don't return "." and ".." unless asked for
         if ( name[0] == wxT('.') &&
diff --git a/tests/file/dir.cpp b/tests/file/dir.cpp
index ae5b81c5d5..fa2b836900 100644
--- a/tests/file/dir.cpp
+++ b/tests/file/dir.cpp
@@ -20,6 +20,16 @@
 #define DIRTEST_FOLDER      wxString("dirTest_folder")
 #define SEP                 wxFileName::GetPathSeparator()
 
+// We can't use wxFileSelectorDefaultWildcardStr from wxCore here, so define
+// our own.
+const wxString WILDCARD_ALL =
+#if defined(__WXMSW__)
+"*.*"
+#else // Unix/Mac
+"*"
+#endif
+;
+
 // ----------------------------------------------------------------------------
 // test fixture
 // ----------------------------------------------------------------------------
@@ -145,6 +155,21 @@ TEST_CASE_METHOD(DirTestCase, "Dir::Traverse", "[dir]")
     wxArrayString files;
     CHECK( wxDir::GetAllFiles(DIRTEST_FOLDER, &files) == 4 );
 
+    // enum all files using an explicit wildcard
+    CHECK(wxDir::GetAllFiles(DIRTEST_FOLDER, &files, WILDCARD_ALL) == 4);
+
+    // enum all files using an explicit wildcard different from WILDCARD_ALL
+    //
+    // broken under Wine, see https://bugs.winehq.org/show_bug.cgi?id=55677
+    if ( !wxIsRunningUnderWine() )
+    {
+        CHECK(wxDir::GetAllFiles(DIRTEST_FOLDER, &files, "d" + WILDCARD_ALL) == 4);
+    }
+    else if (wxDir::GetAllFiles(DIRTEST_FOLDER, &files, "d" + WILDCARD_ALL) == 4)
+    {
+        WARN("PathMatchSpec() seems to work under Wine now");
+    }
+
     // enum all files according to the filter
     CHECK( wxDir::GetAllFiles(DIRTEST_FOLDER, &files, "*.foo") == 1 );
 
@@ -232,3 +257,45 @@ TEST_CASE_METHOD(DirTestCase, "Dir::GetName", "[dir]")
     CHECK( d.GetNameWithSep() == "/" );
 #endif
 }
+
+// Disabled by default test allowing to check the result of matching against
+// the given filter.
+#ifdef __WXMSW__
+
+#include "wx/msw/wrapwin.h"
+#include <shlwapi.h>
+#ifdef __VISUALC__
+    #pragma comment(lib, "shlwapi")
+#endif
+
+#include "wx/crt.h"
+#include "wx/filefn.h"
+
+TEST_CASE("Dir::Match", "[.]")
+{
+    wxString filter;
+    REQUIRE( wxGetEnv("WX_TEST_DIR_FILTER", &filter) );
+
+    static const wxString filenames[] =
+    {
+        "foo",
+        "foo.bar",
+        "foo.bar.baz",
+        ".hidden",
+        ".hidden.ext",
+    };
+
+    // Show the results of matching the pattern using various functions.
+    wxPrintf("%-15s %20s %20s %20s\n",
+             "File", "wxString::Matches", "wxMatchWild", "PathMatchSpec");
+    for ( const auto& fn : filenames )
+    {
+        wxPrintf("%-15s %20d %20d %20d\n",
+                 fn,
+                 fn.Matches(filter),
+                 wxMatchWild(filter, fn),
+                 PathMatchSpec(fn.wc_str(), filter.wc_str()) == TRUE);
+    }
+}
+
+#endif // __WXMSW__