diff --git a/src/Media.cpp b/src/Media.cpp
index 1e8011ac23408d8d95d3bf5265591240e7e5621b..5ca08cc2294be11bd09baaef298e25dbd757ea45 100644
--- a/src/Media.cpp
+++ b/src/Media.cpp
@@ -886,6 +886,7 @@ std::string Media::sortRequest( const QueryParameters* params )
 
     auto sort = params != nullptr ? params->sort : SortingCriteria::Default;
     auto desc = params != nullptr ? params->desc : false;
+    auto descAdded = false;
     switch ( sort )
     {
     case SortingCriteria::Duration:
@@ -902,7 +903,8 @@ std::string Media::sortRequest( const QueryParameters* params )
         desc = !desc; // Make decreasing order default for play count sorting
         break;
     case SortingCriteria::Filename:
-        req += "m.filename";
+        req += sqlite::Tools::sortedStringField("m.filename",desc,true);
+        descAdded = true;
         break;
     case SortingCriteria::LastModificationDate:
         req += "f.last_modification_date";
@@ -911,30 +913,36 @@ std::string Media::sortRequest( const QueryParameters* params )
         req += "f.size";
         break;
     case SortingCriteria::Album:
-        if ( desc == true )
-            req += "alb.title DESC, att.track_number";
+
+        req += sqlite::Tools::sortedStringField("alb.title",desc,false);
+	if ( desc == true )
+            req += ", att.track_number";
         else
-            req += "alb.title, att.track_number";
+            req += ", att.track_number";
+        descAdded = true;
         break;
     case SortingCriteria::Artist:
-        req += "art.name";
+        req += sqlite::Tools::sortedStringField("art.name",desc,false);
+        descAdded = true;
         break;
     case SortingCriteria::TrackId:
-        if ( desc == true )
-            req += "alb.title, att.track_number DESC, att.disc_number";
+        req += sqlite::Tools::sortedStringField("alb.title",false,false);
+	   if ( desc == true )
+            req += ", att.track_number DESC, att.disc_number";
         else
-            req += "alb.title, att.track_number, att.disc_number";
+            req += ", att.track_number, att.disc_number";
+        descAdded = true;
         break;
     default:
         LOG_WARN( "Unsupported sorting criteria, falling back to SortingCriteria::Default (Alpha)" );
         /* fall-through */
     case SortingCriteria::Default:
     case SortingCriteria::Alpha:
-        req += "m.title";
+         req += sqlite::Tools::sortedStringField("m.title",desc,false);
+         descAdded = true;
         break;
     }
-    if ( desc == true && sort != SortingCriteria::Album &&
-         sort != SortingCriteria::TrackId )
+    if ( desc == true && !descAdded)
         req += " DESC";
     return req;
 }
diff --git a/src/database/SqliteTools.h b/src/database/SqliteTools.h
index 95e539c92e5f25cc3b1dba42eb50ddc6321cae86..e04b21e0fd61fc421d361782fcb6b2f7a46567b1 100644
--- a/src/database/SqliteTools.h
+++ b/src/database/SqliteTools.h
@@ -459,7 +459,25 @@ class Tools
          *         sqlite, and a '*' appended
          */
         static std::string sanitizePattern( const std::string& pattern );
+        static std::string sortedStringField( const std::string& field, bool desc, bool hasExt)
+        {
+            auto d = desc ? " DESC":" ASC";
+
+            auto removeExt = "rtrim(rtrim(" + field + ",replace(" + field + ",'.','')),'.')";
+            auto lengthAfterRemoveExtNumber = "length(rtrim(" + removeExt + ",'0123456789'))";
+
+            auto removeLastNumber = "rtrim(" + field + ",'0123456789')";
+            auto removeNumberAndExt  = "trim(" + removeExt + ",'0123456789')";
 
+            auto lastNumberNoExt = "cast(ltrim(" + field + ",rtrim(" + field + ",'0123456789')) as INTEGER)";
+            auto lastNumberAfterRemoveExt = "cast(substr(" + removeExt + "," + lengthAfterRemoveExtNumber + " + 1) as INTEGER) ";
+
+            auto titleNoExtNumber = (hasExt ? removeNumberAndExt : removeLastNumber) + " COLLATE NOCASE " + d;
+            auto lastNumber = (hasExt ? lastNumberAfterRemoveExt : lastNumberNoExt) + d;
+            auto firstNumber  = " cast(" + field + " as INTEGER) " + d;
+
+            return  titleNoExtNumber + "," + firstNumber + " , " + lastNumber; 
+        }
     private:
         template <typename... Args>
         static void executeRequestLocked( sqlite::Connection* dbConnection,
diff --git a/test/unittest/MediaTests.cpp b/test/unittest/MediaTests.cpp
index 01bddb92e528a57a5739b9454d7810173244f158..530e44560a1ea013bfe85ce5390b5d4211229688 100644
--- a/test/unittest/MediaTests.cpp
+++ b/test/unittest/MediaTests.cpp
@@ -867,7 +867,46 @@ TEST_F( Medias, Pagination )
         media = paginator->items( 1, i );
     }
 }
+TEST_F( Medias, SortFilenameStartsWithNumber )
+{
+    auto m1 = std::static_pointer_cast<Media>( ml->addMedia( "9 song.mp3", IMedia::Type::Audio ) );
+    auto m2 = std::static_pointer_cast<Media>( ml->addMedia( "1 song.mp3", IMedia::Type::Audio ) );
+    auto m3 = std::static_pointer_cast<Media>( ml->addMedia( "10 song.mp3", IMedia::Type::Audio ) );
+
+    QueryParameters params { SortingCriteria::Filename, false };
+    auto media = ml->audioFiles( &params )->all();
+    ASSERT_EQ( 3u, media.size() );
+    ASSERT_EQ( m2->id(), media[0]->id() );
+    ASSERT_EQ( m1->id(), media[1]->id() );
+    ASSERT_EQ( m3->id(), media[2]->id() );
 
+    params.desc = true;
+    media = ml->audioFiles( &params )->all();
+    ASSERT_EQ( 3u, media.size() );
+    ASSERT_EQ( m2->id(), media[2]->id() );
+    ASSERT_EQ( m1->id(), media[1]->id() );
+    ASSERT_EQ( m3->id(), media[0]->id() );
+}
+TEST_F( Medias, SortFilenameEndsWithNumber )
+{
+    auto m1 = std::static_pointer_cast<Media>( ml->addMedia( "song9.mp3", IMedia::Type::Audio ) );
+    auto m2 = std::static_pointer_cast<Media>( ml->addMedia( "song1.mp3", IMedia::Type::Audio ) );
+    auto m3 = std::static_pointer_cast<Media>( ml->addMedia( "song10.mp3", IMedia::Type::Audio ) );
+
+    QueryParameters params { SortingCriteria::Filename, false };
+    auto media = ml->audioFiles( &params )->all();
+    ASSERT_EQ( 3u, media.size() );
+    ASSERT_EQ( m2->id(), media[0]->id() );
+    ASSERT_EQ( m1->id(), media[1]->id() );
+    ASSERT_EQ( m3->id(), media[2]->id() );
+
+    params.desc = true;
+    media = ml->audioFiles( &params )->all();
+    ASSERT_EQ( 3u, media.size() );
+    ASSERT_EQ( m2->id(), media[2]->id() );
+    ASSERT_EQ( m1->id(), media[1]->id() );
+    ASSERT_EQ( m3->id(), media[0]->id() );
+}
 TEST_F( Medias, SortFilename )
 {
     auto m1 = std::static_pointer_cast<Media>( ml->addMedia( "AAAAB.mp3", IMedia::Type::Audio ) );