diff --git a/packages/core-components/src/layout/Sidebar/Items.test.tsx b/packages/core-components/src/layout/Sidebar/Items.test.tsx
index eafbf3827e..9479180180 100644
--- a/packages/core-components/src/layout/Sidebar/Items.test.tsx
+++ b/packages/core-components/src/layout/Sidebar/Items.test.tsx
@@ -15,7 +15,11 @@
  */
 
 import React from 'react';
-import { renderInTestApp } from '@backstage/test-utils';
+import {
+  MockAnalyticsApi,
+  TestApiProvider,
+  renderInTestApp,
+} from '@backstage/test-utils';
 import { createEvent, fireEvent, screen } from '@testing-library/react';
 import userEvent from '@testing-library/user-event';
 import HomeIcon from '@material-ui/icons/Home';
@@ -24,6 +28,7 @@ import { Sidebar } from './Bar';
 import { SidebarItem, SidebarSearchField, SidebarExpandButton } from './Items';
 import { renderHook } from '@testing-library/react-hooks';
 import { makeStyles } from '@material-ui/core/styles';
+import { analyticsApiRef } from '@backstage/core-plugin-api';
 
 const useStyles = makeStyles({
   spotlight: {
@@ -31,27 +36,50 @@ const useStyles = makeStyles({
   },
 });
 
+let analyticsApiMock: MockAnalyticsApi;
+
+const handleSidebarItemClick = jest.fn();
+
 async function renderSidebar() {
   const { result } = renderHook(() => useStyles());
 
   await renderInTestApp(
-    <Sidebar>
-      <SidebarSearchField onSearch={() => {}} to="/search" />
-      <SidebarItem text="Home" icon={HomeIcon} to="./" />
-      <SidebarItem
-        icon={CreateComponentIcon}
-        onClick={() => {}}
-        text="Create..."
-        className={result.current.spotlight}
-      />
-      <SidebarExpandButton />
-    </Sidebar>,
+    <TestApiProvider apis={[[analyticsApiRef, analyticsApiMock]]}>
+      <Sidebar>
+        <SidebarSearchField onSearch={() => {}} to="/search" />
+        <SidebarItem text="Home" icon={HomeIcon} to="./" />
+        <SidebarItem
+          icon={CreateComponentIcon}
+          onClick={handleSidebarItemClick}
+          text="Create..."
+          className={result.current.spotlight}
+        />
+        <SidebarItem
+          icon={CreateComponentIcon}
+          to="/docs"
+          onClick={handleSidebarItemClick}
+          text="Docs"
+          className={result.current.spotlight}
+        />
+        <SidebarItem
+          icon={CreateComponentIcon}
+          to="/explore"
+          onClick={handleSidebarItemClick}
+          text="Explore"
+          className={result.current.spotlight}
+          noTrack
+        />
+        <SidebarExpandButton />
+      </Sidebar>
+    </TestApiProvider>,
   );
   await userEvent.hover(screen.getByTestId('sidebar-root'));
 }
 
 describe('Items', () => {
   beforeEach(async () => {
+    jest.clearAllMocks();
+    analyticsApiMock = new MockAnalyticsApi();
     await renderSidebar();
   });
 
@@ -73,6 +101,40 @@ describe('Items', () => {
         await screen.findByRole('button', { name: /create/i }),
       ).toHaveStyle(`background-color: transparent`);
     });
+
+    it('should send button clicks to analytics', async () => {
+      await userEvent.click(
+        await screen.findByRole('button', { name: /create/i }),
+      );
+      expect(handleSidebarItemClick).toHaveBeenCalledTimes(1);
+      expect(analyticsApiMock.getEvents()).toHaveLength(1);
+      expect(analyticsApiMock.getEvents()[0]).toMatchObject({
+        action: 'click',
+        subject: 'Create...',
+        context: { routeRef: 'unknown', pluginId: 'root', extension: 'App' },
+        attributes: { to: '/' },
+      });
+    });
+
+    it('should send link clicks to analytics', async () => {
+      await userEvent.click(await screen.findByRole('link', { name: /docs/i }));
+      expect(handleSidebarItemClick).toHaveBeenCalledTimes(1);
+      expect(analyticsApiMock.getEvents()).toHaveLength(1);
+      expect(analyticsApiMock.getEvents()[0]).toMatchObject({
+        action: 'click',
+        subject: 'Docs',
+        context: { routeRef: 'unknown', pluginId: 'root', extension: 'App' },
+        attributes: { to: '/docs' },
+      });
+    });
+
+    it('should not send clicks to analytics when tracking is disabled', async () => {
+      await userEvent.click(
+        await screen.findByRole('link', { name: /explore/i }),
+      );
+      expect(handleSidebarItemClick).toHaveBeenCalledTimes(1);
+      expect(analyticsApiMock.getEvents()).toHaveLength(0);
+    });
   });
   describe('SidebarSearchField', () => {
     it('should be defaultPrevented when enter is pressed', async () => {
diff --git a/packages/core-components/src/layout/Sidebar/Items.tsx b/packages/core-components/src/layout/Sidebar/Items.tsx
index 00d1871947..96c2b382e7 100644
--- a/packages/core-components/src/layout/Sidebar/Items.tsx
+++ b/packages/core-components/src/layout/Sidebar/Items.tsx
@@ -13,7 +13,11 @@
  * See the License for the specific language governing permissions and
  * limitations under the License.
  */
-import { IconComponent, useElementFilter } from '@backstage/core-plugin-api';
+import {
+  IconComponent,
+  useAnalytics,
+  useElementFilter,
+} from '@backstage/core-plugin-api';
 import { BackstageTheme } from '@backstage/theme';
 import Badge from '@material-ui/core/Badge';
 import Box from '@material-ui/core/Box';
@@ -38,6 +42,7 @@ import React, {
   forwardRef,
   KeyboardEventHandler,
   ReactNode,
+  useCallback,
   useContext,
   useMemo,
   useState,
@@ -264,6 +269,8 @@ type SidebarItemBaseProps = {
   hasSubmenu?: boolean;
   disableHighlight?: boolean;
   className?: string;
+  noTrack?: boolean;
+  onClick?: (ev: React.MouseEvent) => void;
 };
 
 type SidebarItemButtonProps = SidebarItemBaseProps & {
@@ -362,6 +369,7 @@ const SidebarItemBase = forwardRef<any, SidebarItemProps>((props, ref) => {
     hasSubmenu = false,
     disableHighlight = false,
     onClick,
+    noTrack,
     children,
     className,
     ...navLinkProps
@@ -424,9 +432,33 @@ const SidebarItemBase = forwardRef<any, SidebarItemProps>((props, ref) => {
     ),
   };
 
+  const analyticsApi = useAnalytics();
+  const { pathname: to } = useResolvedPath(
+    !isButtonItem(props) && props.to ? props.to : '',
+  );
+
+  const handleClick = useCallback(
+    (event: React.MouseEvent<HTMLAnchorElement | HTMLButtonElement>) => {
+      if (!noTrack) {
+        const action = 'click';
+        const subject = text ?? 'Sidebar Item';
+        const options = to ? { attributes: { to } } : undefined;
+        analyticsApi.captureEvent(action, subject, options);
+      }
+      onClick?.(event);
+    },
+    [analyticsApi, text, to, noTrack, onClick],
+  );
+
   if (isButtonItem(props)) {
     return (
-      <Button role="button" aria-label={text} {...childProps} ref={ref}>
+      <Button
+        role="button"
+        aria-label={text}
+        {...childProps}
+        ref={ref}
+        onClick={handleClick}
+      >
         {content}
       </Button>
     );
@@ -440,6 +472,7 @@ const SidebarItemBase = forwardRef<any, SidebarItemProps>((props, ref) => {
       ref={ref}
       aria-label={text ? text : props.to}
       {...navLinkProps}
+      onClick={handleClick}
     >
       {content}
     </WorkaroundNavLink>