diff --git a/osu.Game/Extensions/DrawableExtensions.cs b/osu.Game/Extensions/DrawableExtensions.cs
index 5b92600cd1..46105218c5 100644
--- a/osu.Game/Extensions/DrawableExtensions.cs
+++ b/osu.Game/Extensions/DrawableExtensions.cs
@@ -82,11 +82,12 @@ namespace osu.Game.Extensions
         }
 
         /// <summary>
-        /// Keeps the drawable upright no matter the Rotation of its parents.
+        /// Keeps the drawable upright and prevents it from being scaled or flipped with its Parent.
         /// </summary>
         /// <param name="drawable">The drawable.</param>
-        public static void KeepUpright(this Drawable drawable)
+        public static void KeepUprightAndUnstretched(this Drawable drawable)
         {
+            // Fix the rotation
             var result = drawable.Parent.DrawInfo;
             var scale = result.Matrix.ExtractScale();
             var rotation = new Matrix3(
@@ -94,9 +95,30 @@ namespace osu.Game.Extensions
             result.Matrix.Row1 / scale.Y,
             new Vector3(0.0f, 0.0f, 1.0f)
             );
-            float angle = MathF.Atan2(rotation.M12, rotation.M11);
+            rotation.Invert();
+            float angle = MathF.Atan(rotation.M12 / rotation.M11);
             angle *= (360 / (2 * MathF.PI));
-            drawable.Rotation = -angle;
+            drawable.Rotation = angle;
+
+            // Fix the scale (includes flip)
+            var containerOriginToSpaceOrigin = new Matrix3(
+                new Vector3(1.0f, 0.0f, 0.0f),
+                new Vector3(0.0f, 1.0f, 0.0f),
+                new Vector3(drawable.DrawSize.X / 2, drawable.DrawSize.Y / 2, 1.0f)
+                );
+            var containerOriginToSpaceOriginInverse = containerOriginToSpaceOrigin;
+            containerOriginToSpaceOriginInverse.Invert();
+            Matrix3 rotatedBack = (containerOriginToSpaceOriginInverse * (rotation * (containerOriginToSpaceOrigin * result.Matrix)));
+
+            bool xFliped = rotation.M11 < 0;
+            bool yFliped = rotation.M22 < 0;
+
+            var rotatedBackScale = rotatedBack.ExtractScale();
+
+            drawable.Scale = new Vector2(
+                (xFliped ? -1 : 1) / rotatedBackScale.X,
+                (yFliped ? -1 : 1) / rotatedBackScale.Y
+            );
         }
 
     }
diff --git a/osu.Game/Screens/Play/HUD/DefaultSongProgress.cs b/osu.Game/Screens/Play/HUD/DefaultSongProgress.cs
index 96a6c56860..9ed99ab5f6 100644
--- a/osu.Game/Screens/Play/HUD/DefaultSongProgress.cs
+++ b/osu.Game/Screens/Play/HUD/DefaultSongProgress.cs
@@ -5,6 +5,7 @@ using System.Collections.Generic;
 using osu.Framework.Allocation;
 using osu.Framework.Bindables;
 using osu.Framework.Graphics;
+using osu.Framework.Graphics.Shapes;
 using osu.Game.Configuration;
 using osu.Game.Graphics;
 using osu.Game.Rulesets.Objects;
@@ -16,7 +17,6 @@ namespace osu.Game.Screens.Play.HUD
 {
     public class DefaultSongProgress : SongProgress
     {
-        private const float info_height = 20;
         private const float bottom_bar_height = 5;
         private const float graph_height = SquareGraph.Column.WIDTH * 6;
         private const float handle_height = 18;
@@ -67,7 +67,6 @@ namespace osu.Game.Screens.Play.HUD
                     Origin = Anchor.BottomLeft,
                     Anchor = Anchor.BottomLeft,
                     RelativeSizeAxes = Axes.X,
-                    Height = info_height,
                 },
                 graph = new SongProgressGraph
                 {
@@ -180,7 +179,7 @@ namespace osu.Game.Screens.Play.HUD
         protected override void Update()
         {
             base.Update();
-            Height = bottom_bar_height + graph_height + handle_size.Y + info_height - graph.Y;
+            Height = bottom_bar_height + graph_height + handle_size.Y + info.Height - graph.Y;
         }
 
         private void updateBarVisibility()
diff --git a/osu.Game/Screens/Play/HUD/SongProgressInfo.cs b/osu.Game/Screens/Play/HUD/SongProgressInfo.cs
index 520d0c661d..656498fc43 100644
--- a/osu.Game/Screens/Play/HUD/SongProgressInfo.cs
+++ b/osu.Game/Screens/Play/HUD/SongProgressInfo.cs
@@ -46,6 +46,7 @@ namespace osu.Game.Screens.Play.HUD
             if (clock != null)
                 gameplayClock = clock;
 
+            AutoSizeAxes = Axes.Y;
             Children = new Drawable[]
             {
                 new Container
@@ -138,9 +139,9 @@ namespace osu.Game.Screens.Play.HUD
 
         private void keepTextSpritesUpright()
         {
-            timeCurrent.OnUpdate += (timeCurrent) => { Extensions.DrawableExtensions.KeepUpright(timeCurrent); };
-            progress.OnUpdate += (timeCurrent) => { Extensions.DrawableExtensions.KeepUpright(timeCurrent); };
-            timeLeft.OnUpdate += (timeCurrent) => { Extensions.DrawableExtensions.KeepUpright(timeCurrent); };
+            timeCurrent.OnUpdate += (timeCurrent) => { Extensions.DrawableExtensions.KeepUprightAndUnstretched(timeCurrent); };
+            progress.OnUpdate += (timeCurrent) => { Extensions.DrawableExtensions.KeepUprightAndUnstretched(timeCurrent); };
+            timeLeft.OnUpdate += (timeCurrent) => { Extensions.DrawableExtensions.KeepUprightAndUnstretched(timeCurrent); };
         }
 
     }