diff --git a/frappe/desk/doctype/todo/todo_list.js b/frappe/desk/doctype/todo/todo_list.js
index 47cb7bd1f6..6200e85dca 100644
--- a/frappe/desk/doctype/todo/todo_list.js
+++ b/frappe/desk/doctype/todo/todo_list.js
@@ -10,21 +10,14 @@ frappe.listview_settings['ToDo'] = {
 	},
 	hide_name_column: true,
 	refresh: function(me) {
-		// override assigned to me by owner
 		if (me.todo_sidebar_setup) return;
 
-		me.page.sidebar.find(".assigned-to-me a").off("click").on("click", function() {
-			me.filter_area.remove("assigned_by");
-			me.filter_area.add([[me.doctype, "owner", '=', frappe.session.user]]);
-		});
-
 		// add assigned by me
 		me.page.add_sidebar_item(__("Assigned By Me"), function() {
-			me.filter_area.remove("owner");
 			me.filter_area.add([[me.doctype, "assigned_by", '=', frappe.session.user]]);
-		}, ".assigned-to-me");
+		}, ('.list-link[data-view="Kanban"]'));
 
 		me.todo_sidebar_setup = true;
 	},
 	add_fields: ["reference_type", "reference_name"],
-}
+}
\ No newline at end of file
diff --git a/frappe/desk/listview.py b/frappe/desk/listview.py
index 8d439f228a..a05a3e7f04 100644
--- a/frappe/desk/listview.py
+++ b/frappe/desk/listview.py
@@ -24,3 +24,10 @@ def set_list_settings(doctype, values):
 		frappe.clear_messages()
 	doc.update(json.loads(values))
 	doc.save()
+
+@frappe.whitelist()
+def get_user_assignments_and_count():
+	user_list = frappe.get_list("User", filters={"user_type": "System User"})
+	assignment_data = sorted([{"count":frappe.db.count('ToDo', filters = {'reference_type': 'Issue', 'owner': user['name'], 'status': 'Open'}),
+						"name": user['name']} for user in user_list], key=lambda k: k['count'], reverse = True)
+	return assignment_data
\ No newline at end of file
diff --git a/frappe/public/js/frappe/list/list_sidebar.html b/frappe/public/js/frappe/list/list_sidebar.html
index 48ed21765b..619fa66277 100644
--- a/frappe/public/js/frappe/list/list_sidebar.html
+++ b/frappe/public/js/frappe/list/list_sidebar.html
@@ -45,8 +45,12 @@
 			</ul>
 		</div>
 	</li>
-	<li class="assigned-to-me">
-		<a>{%= __("Assigned To Me") %}</a>
+	<li class="assigned-to">
+		<a class = "dropdown-toggle" data-toggle="dropdown" aria-haspopup="true" aria-expanded="false">
+			{%= __("Assigned To") %} <span class="caret"></span>
+		</a>
+		<ul class="dropdown-menu assigned-dropdown" style="max-height: 300px; overflow-y: auto;">
+		</ul>
 	</li>
 	{% if(frappe.help.has_help(doctype)) { %}
 	<li><a class="help-link" data-doctype="{{ doctype }}">{{ __("Help") }}</a></li>
diff --git a/frappe/public/js/frappe/list/list_sidebar.js b/frappe/public/js/frappe/list/list_sidebar.js
index 20f1f030d4..9f5ebfb2a7 100644
--- a/frappe/public/js/frappe/list/list_sidebar.js
+++ b/frappe/public/js/frappe/list/list_sidebar.js
@@ -26,7 +26,7 @@ frappe.views.ListSidebar = class ListSidebar {
 
 		this.setup_reports();
 		this.setup_list_filter();
-		this.setup_assigned_to_me();
+		this.setup_assigned_to();
 		this.setup_views();
 		this.setup_kanban_boards();
 		this.setup_calendar_view();
@@ -216,12 +216,35 @@ frappe.views.ListSidebar = class ListSidebar {
 		});
 	}
 
-	setup_assigned_to_me() {
-		this.page.sidebar.find(".assigned-to-me a").on("click", () => {
-			this.list_view.filter_area.add(this.list_view.doctype, "_assign", "like", `%${frappe.session.user}%`);
+	setup_assigned_to() {
+		let dropdown = this.page.sidebar.find('.assigned-dropdown');
+		if(this.doctype === 'ToDo') {
+			$('.assigned-to').remove();
+		}
+		frappe.call('frappe.desk.listview.get_user_assignments_and_count').then((data) => {
+			let current_user_count = data.message.find(user => user.name === frappe.session.user).count;
+			this.get_html_for_assigned(frappe.session.user, current_user_count).appendTo(dropdown);
+			let user_list = data.message.filter(user => !['Guest', frappe.session.user, 'Administrator'].includes(user.name));
+			user_list.forEach((user) => {
+				this.get_html_for_assigned(user.name, user.count).appendTo(dropdown);
+			});
+			$(".assigned-dropdown li a").on("click", (e) => {
+				let assigned_user = $(e.currentTarget).find($('.assigned-user')).text();
+				if(assigned_user === 'Me') assigned_user = frappe.session.user;
+				this.list_view.filter_area.remove('_assign');
+				this.list_view.filter_area.add(this.list_view.doctype, "_assign", "like", `%${assigned_user}%`);
+			});
 		});
 	}
 
+	get_html_for_assigned(name, count) {
+		if (name === frappe.session.user) name='Me';
+		if (count > 99) count='99+';
+		let html = $('<li class="assigned"><a class="badge-hover" role="assigned-item"><span class="assigned-user">' 
+					+ name + '</span><span class="badge pull-right" style="position:relative">' + count + '</span></a></li>');
+		return html;
+	}
+
 	setup_upgrade_box() {
 		let upgrade_list = $(`<ul class="list-unstyled sidebar-menu"></ul>`).appendTo(this.sidebar);