diff --git a/.changeset/timeline-clip-sidebar-options.md b/.changeset/timeline-clip-sidebar-options.md
new file mode 100644
index 00000000000..cef6fe7fdd2
--- /dev/null
+++ b/.changeset/timeline-clip-sidebar-options.md
@@ -0,0 +1,5 @@
+---
+'@primer/react': minor
+---
+
+Timeline: Update `clipSidebar` prop to accept `'start'`, `'end'`, or `'both'` in addition to `boolean`. Use `'start'` to only clip the top, `'end'` to only clip the bottom, or `'both'`/`true` to clip both ends.
diff --git a/.playwright/snapshots/components/Timeline.test.ts-snapshots/Timeline-Clip-Sidebar-End-dark-colorblind-linux.png b/.playwright/snapshots/components/Timeline.test.ts-snapshots/Timeline-Clip-Sidebar-End-dark-colorblind-linux.png
new file mode 100644
index 00000000000..5a46c33fd92
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diff --git a/.playwright/snapshots/components/Timeline.test.ts-snapshots/Timeline-Clip-Sidebar-End-dark-dimmed-linux.png b/.playwright/snapshots/components/Timeline.test.ts-snapshots/Timeline-Clip-Sidebar-End-dark-dimmed-linux.png
new file mode 100644
index 00000000000..faf00037b79
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diff --git a/.playwright/snapshots/components/Timeline.test.ts-snapshots/Timeline-Clip-Sidebar-End-dark-high-contrast-linux.png b/.playwright/snapshots/components/Timeline.test.ts-snapshots/Timeline-Clip-Sidebar-End-dark-high-contrast-linux.png
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diff --git a/.playwright/snapshots/components/Timeline.test.ts-snapshots/Timeline-Clip-Sidebar-End-light-colorblind-linux.png b/.playwright/snapshots/components/Timeline.test.ts-snapshots/Timeline-Clip-Sidebar-End-light-colorblind-linux.png
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new file mode 100644
index 00000000000..1e9ead71ceb
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diff --git a/.playwright/snapshots/components/Timeline.test.ts-snapshots/Timeline-Clip-Sidebar-Start-light-linux.png b/.playwright/snapshots/components/Timeline.test.ts-snapshots/Timeline-Clip-Sidebar-Start-light-linux.png
new file mode 100644
index 00000000000..ceb8cf3d8c0
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diff --git a/.playwright/snapshots/components/Timeline.test.ts-snapshots/Timeline-Clip-Sidebar-Start-light-tritanopia-linux.png b/.playwright/snapshots/components/Timeline.test.ts-snapshots/Timeline-Clip-Sidebar-Start-light-tritanopia-linux.png
new file mode 100644
index 00000000000..ceb8cf3d8c0
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diff --git a/e2e/components/Timeline.test.ts b/e2e/components/Timeline.test.ts
index ed8a8d4953a..316d88faaf8 100644
--- a/e2e/components/Timeline.test.ts
+++ b/e2e/components/Timeline.test.ts
@@ -11,6 +11,14 @@ const stories = [
     title: 'Clip Sidebar',
     id: 'components-timeline-features--clip-sidebar',
   },
+  {
+    title: 'Clip Sidebar Start',
+    id: 'components-timeline-features--clip-sidebar-start',
+  },
+  {
+    title: 'Clip Sidebar End',
+    id: 'components-timeline-features--clip-sidebar-end',
+  },
   {
     title: 'Condensed Items',
     id: 'components-timeline-features--condensed-items',
diff --git a/packages/react/src/Timeline/Timeline.docs.json b/packages/react/src/Timeline/Timeline.docs.json
index 35f24010491..159297b9183 100644
--- a/packages/react/src/Timeline/Timeline.docs.json
+++ b/packages/react/src/Timeline/Timeline.docs.json
@@ -10,6 +10,12 @@
     {
       "id": "components-timeline-features--clip-sidebar"
     },
+    {
+      "id": "components-timeline-features--clip-sidebar-start"
+    },
+    {
+      "id": "components-timeline-features--clip-sidebar-end"
+    },
     {
       "id": "components-timeline-features--condensed-items"
     },
@@ -24,8 +30,8 @@
   "props": [
     {
       "name": "clipSidebar",
-      "type": "boolean",
-      "description": "Hides the sidebar above the first Timeline.Item and below the last Timeline.Item."
+      "type": "| boolean | 'start' | 'end' | 'both'",
+      "description": "Controls which ends of the sidebar are clipped. When set to `true` or `'both'`, hides the sidebar above the first and below the last Timeline.Item. Use `'start'` to only clip the top or `'end'` to only clip the bottom."
     }
   ],
   "subcomponents": [
diff --git a/packages/react/src/Timeline/Timeline.features.stories.tsx b/packages/react/src/Timeline/Timeline.features.stories.tsx
index c924b48ee7f..b997ad10baf 100644
--- a/packages/react/src/Timeline/Timeline.features.stories.tsx
+++ b/packages/react/src/Timeline/Timeline.features.stories.tsx
@@ -34,6 +34,40 @@ export const ClipSidebar = () => (
   </Timeline>
 )
 
+export const ClipSidebarStart = () => (
+  <Timeline clipSidebar="start">
+    <Timeline.Item>
+      <Timeline.Badge>
+        <Octicon icon={GitCommitIcon} aria-label="Commit" />
+      </Timeline.Badge>
+      <Timeline.Body>This is a message</Timeline.Body>
+    </Timeline.Item>
+    <Timeline.Item>
+      <Timeline.Badge>
+        <Octicon icon={GitCommitIcon} aria-label="Commit" />
+      </Timeline.Badge>
+      <Timeline.Body>This is a message</Timeline.Body>
+    </Timeline.Item>
+  </Timeline>
+)
+
+export const ClipSidebarEnd = () => (
+  <Timeline clipSidebar="end">
+    <Timeline.Item>
+      <Timeline.Badge>
+        <Octicon icon={GitCommitIcon} aria-label="Commit" />
+      </Timeline.Badge>
+      <Timeline.Body>This is a message</Timeline.Body>
+    </Timeline.Item>
+    <Timeline.Item>
+      <Timeline.Badge>
+        <Octicon icon={GitCommitIcon} aria-label="Commit" />
+      </Timeline.Badge>
+      <Timeline.Body>This is a message</Timeline.Body>
+    </Timeline.Item>
+  </Timeline>
+)
+
 export const CondensedItems = () => (
   <Timeline>
     <Timeline.Item condensed>
diff --git a/packages/react/src/Timeline/Timeline.module.css b/packages/react/src/Timeline/Timeline.module.css
index f90a195d71b..a841e6b909d 100644
--- a/packages/react/src/Timeline/Timeline.module.css
+++ b/packages/react/src/Timeline/Timeline.module.css
@@ -2,7 +2,8 @@
   display: flex;
   flex-direction: column;
 
-  &:where([data-clip-sidebar]) {
+  &:where([data-clip-sidebar='start']),
+  &:where([data-clip-sidebar='both']) {
     .TimelineItem:first-child {
       padding-top: 0;
 
@@ -10,7 +11,10 @@
         top: var(--base-size-12);
       }
     }
+  }
 
+  &:where([data-clip-sidebar='end']),
+  &:where([data-clip-sidebar='both']) {
     .TimelineItem:last-child {
       padding-bottom: 0;
 
diff --git a/packages/react/src/Timeline/Timeline.stories.tsx b/packages/react/src/Timeline/Timeline.stories.tsx
index ceb1c5d6db3..fd03321f503 100644
--- a/packages/react/src/Timeline/Timeline.stories.tsx
+++ b/packages/react/src/Timeline/Timeline.stories.tsx
@@ -72,3 +72,10 @@ Playground.args = {
   clipSidebar: false,
   condensed: false,
 }
+
+Playground.argTypes = {
+  clipSidebar: {
+    control: {type: 'select'},
+    options: [false, true, 'start', 'end', 'both'],
+  },
+}
diff --git a/packages/react/src/Timeline/Timeline.tsx b/packages/react/src/Timeline/Timeline.tsx
index 772acbbfff8..00ccee8345b 100644
--- a/packages/react/src/Timeline/Timeline.tsx
+++ b/packages/react/src/Timeline/Timeline.tsx
@@ -2,17 +2,24 @@ import {clsx} from 'clsx'
 import React from 'react'
 import classes from './Timeline.module.css'
 
-type StyledTimelineProps = {clipSidebar?: boolean; className?: string}
+type StyledTimelineProps = {clipSidebar?: boolean | 'start' | 'end' | 'both'; className?: string}
 
 export type TimelineProps = StyledTimelineProps & React.ComponentPropsWithoutRef<'div'>
 
+function resolveClipSidebar(clipSidebar: TimelineProps['clipSidebar']): string | undefined {
+  if (clipSidebar === true || clipSidebar === 'both') return 'both'
+  if (clipSidebar === 'start' || clipSidebar === 'end') return clipSidebar
+  return undefined
+}
+
 const Timeline = React.forwardRef<HTMLDivElement, TimelineProps>(({clipSidebar, className, ...props}, forwardRef) => {
+  const resolvedClipSidebar = resolveClipSidebar(clipSidebar)
   return (
     <div
       {...props}
       className={clsx(className, classes.Timeline)}
       ref={forwardRef}
-      data-clip-sidebar={clipSidebar ? '' : undefined}
+      data-clip-sidebar={resolvedClipSidebar}
     />
   )
 })
diff --git a/packages/react/src/Timeline/__tests__/Timeline.test.tsx b/packages/react/src/Timeline/__tests__/Timeline.test.tsx
index 30715ddbef7..11a575a3e09 100644
--- a/packages/react/src/Timeline/__tests__/Timeline.test.tsx
+++ b/packages/react/src/Timeline/__tests__/Timeline.test.tsx
@@ -7,9 +7,34 @@ import classes from '../Timeline.module.css'
 describe('Timeline', () => {
   implementsClassName(Timeline, classes.Timeline)
 
-  it('renders with clipSidebar prop', () => {
+  it('renders with clipSidebar prop (boolean)', () => {
     const {container} = render(<Timeline clipSidebar />)
-    expect(container).toMatchSnapshot()
+    expect(container.firstChild).toHaveAttribute('data-clip-sidebar', 'both')
+  })
+
+  it('renders with clipSidebar="both"', () => {
+    const {container} = render(<Timeline clipSidebar="both" />)
+    expect(container.firstChild).toHaveAttribute('data-clip-sidebar', 'both')
+  })
+
+  it('renders with clipSidebar="start"', () => {
+    const {container} = render(<Timeline clipSidebar="start" />)
+    expect(container.firstChild).toHaveAttribute('data-clip-sidebar', 'start')
+  })
+
+  it('renders with clipSidebar="end"', () => {
+    const {container} = render(<Timeline clipSidebar="end" />)
+    expect(container.firstChild).toHaveAttribute('data-clip-sidebar', 'end')
+  })
+
+  it('does not render data-clip-sidebar when clipSidebar is false', () => {
+    const {container} = render(<Timeline clipSidebar={false} />)
+    expect(container.firstChild).not.toHaveAttribute('data-clip-sidebar')
+  })
+
+  it('does not render data-clip-sidebar when clipSidebar is not provided', () => {
+    const {container} = render(<Timeline />)
+    expect(container.firstChild).not.toHaveAttribute('data-clip-sidebar')
   })
 })
 
diff --git a/packages/react/src/Timeline/__tests__/Timeline.types.test.tsx b/packages/react/src/Timeline/__tests__/Timeline.types.test.tsx
index 9e723c6e98d..7d83cad1333 100644
--- a/packages/react/src/Timeline/__tests__/Timeline.types.test.tsx
+++ b/packages/react/src/Timeline/__tests__/Timeline.types.test.tsx
@@ -12,6 +12,28 @@ export function shouldAcceptCallWithNoProps() {
   )
 }
 
+export function shouldAcceptClipSidebarValues() {
+  return (
+    <>
+      <Timeline clipSidebar />
+      <Timeline clipSidebar={true} />
+      <Timeline clipSidebar={false} />
+      <Timeline clipSidebar="start" />
+      <Timeline clipSidebar="end" />
+      <Timeline clipSidebar="both" />
+    </>
+  )
+}
+
+export function shouldNotAcceptInvalidClipSidebarValues() {
+  return (
+    <>
+      {/* @ts-expect-error invalid string value should not be accepted */}
+      <Timeline clipSidebar="invalid" />
+    </>
+  )
+}
+
 export function shouldNotAcceptSystemProps() {
   return (
     <>
diff --git a/packages/react/src/Timeline/__tests__/__snapshots__/Timeline.test.tsx.snap b/packages/react/src/Timeline/__tests__/__snapshots__/Timeline.test.tsx.snap
index 07e7ebe6f73..542aaab3ecf 100644
--- a/packages/react/src/Timeline/__tests__/__snapshots__/Timeline.test.tsx.snap
+++ b/packages/react/src/Timeline/__tests__/__snapshots__/Timeline.test.tsx.snap
@@ -1,14 +1,5 @@
 // Vitest Snapshot v1, https://vitest.dev/guide/snapshot.html
 
-exports[`Timeline > renders with clipSidebar prop 1`] = `
-<div>
-  <div
-    class="prc-Timeline-Timeline-T476g"
-    data-clip-sidebar=""
-  />
-</div>
-`;
-
 exports[`Timeline.Item > renders with condensed prop 1`] = `
 <div>
   <div