diff --git a/.changeset/gorgeous-steaks-report.md b/.changeset/gorgeous-steaks-report.md
new file mode 100644
index 0000000000..2df79ac6f6
--- /dev/null
+++ b/.changeset/gorgeous-steaks-report.md
@@ -0,0 +1,6 @@
+---
+'@emotion/cache': minor
+'@emotion/sheet': minor
+---
+
+Accept new `prepend` option to allow for adding style tags at the beginning of the specified DOM container.
diff --git a/packages/cache/README.md b/packages/cache/README.md
index 0b94e1ffe2..be76d90ecb 100644
--- a/packages/cache/README.md
+++ b/packages/cache/README.md
@@ -56,3 +56,9 @@ The prefix before class names. It will also be set as the value of the `data-emo
 `HTMLElement`
 
 A DOM node that emotion will insert all of its style tags into. This is useful for inserting styles into iframes.
+
+### `prepend`
+
+`boolean`
+
+A string representing whether to prepend rather than append style tags into the specified container DOM node.
diff --git a/packages/cache/src/index.js b/packages/cache/src/index.js
index a8caad7a1b..f93998e60b 100644
--- a/packages/cache/src/index.js
+++ b/packages/cache/src/index.js
@@ -19,7 +19,8 @@ export type Options = {
   prefix?: PrefixOption,
   key?: string,
   container?: HTMLElement,
-  speedy?: boolean
+  speedy?: boolean,
+  prepend?: boolean
 }
 
 let rootServerStylisCache = {}
@@ -240,7 +241,8 @@ let createCache = (options?: Options): EmotionCache => {
       key,
       container,
       nonce: options.nonce,
-      speedy: options.speedy
+      speedy: options.speedy,
+      prepend: options.prepend
     }),
     nonce: options.nonce,
     inserted,
diff --git a/packages/cache/types/index.d.ts b/packages/cache/types/index.d.ts
index a9a9ca8fd5..ef317ac573 100644
--- a/packages/cache/types/index.d.ts
+++ b/packages/cache/types/index.d.ts
@@ -12,6 +12,7 @@ export interface Options {
   key?: string
   container?: HTMLElement
   speedy?: boolean
+  prepend?: boolean
 }
 
 export default function createCache(options?: Options): EmotionCache
diff --git a/packages/sheet/__tests__/__snapshots__/index.js.snap b/packages/sheet/__tests__/__snapshots__/index.js.snap
index 322157e694..0a281a3b4f 100644
--- a/packages/sheet/__tests__/__snapshots__/index.js.snap
+++ b/packages/sheet/__tests__/__snapshots__/index.js.snap
@@ -1,5 +1,28 @@
 // Jest Snapshot v1, https://goo.gl/fbAQLP
 
+exports[`StyleSheet should accept prepend option 1`] = `
+<html>
+  <head>
+    <style
+      data-emotion=""
+    >
+      
+      html { color: hotpink; }
+    </style>
+    <style
+      data-emotion=""
+    >
+      
+      * { box-sizing: border-box; }
+    </style>
+    <style
+      id="other"
+    />
+  </head>
+  <body />
+</html>
+`;
+
 exports[`StyleSheet should insert a rule into the DOM when not in speedy 1`] = `
 <html>
   <head>
diff --git a/packages/sheet/__tests__/index.js b/packages/sheet/__tests__/index.js
index 35ada5c952..1caf083f1a 100644
--- a/packages/sheet/__tests__/index.js
+++ b/packages/sheet/__tests__/index.js
@@ -3,6 +3,7 @@ import { safeQuerySelector } from 'test-utils'
 import { StyleSheet } from '@emotion/sheet'
 
 const rule = 'html { color: hotpink; }'
+const rule2 = '* { box-sizing: border-box; }'
 
 let defaultOptions = {
   key: '',
@@ -110,4 +111,19 @@ describe('StyleSheet', () => {
     expect(sheet.tags[0].sheet.cssRules[0]).toBeInstanceOf(window.CSSImportRule)
     sheet.flush()
   })
+
+  it('should accept prepend option', () => {
+    const head = safeQuerySelector('head')
+    const otherStyle = document.createElement('style')
+    otherStyle.setAttribute('id', 'other')
+    head.appendChild(otherStyle)
+
+    const sheet = new StyleSheet({ ...defaultOptions, prepend: true })
+    sheet.insert(rule)
+    sheet.insert(rule2)
+    expect(document.documentElement).toMatchSnapshot()
+
+    sheet.flush()
+    head.removeChild(otherStyle)
+  })
 })
diff --git a/packages/sheet/src/index.js b/packages/sheet/src/index.js
index c7e5f41ef3..ff4b93add1 100644
--- a/packages/sheet/src/index.js
+++ b/packages/sheet/src/index.js
@@ -43,7 +43,8 @@ export type Options = {
   nonce?: string,
   key: string,
   container: HTMLElement,
-  speedy?: boolean
+  speedy?: boolean,
+  prepend?: boolean
 }
 
 function createStyleElement(options: {
@@ -66,6 +67,7 @@ export class StyleSheet {
   container: HTMLElement
   key: string
   nonce: string | void
+  prepend: boolean | void
   before: Element | null
   constructor(options: Options) {
     this.isSpeedy =
@@ -78,6 +80,7 @@ export class StyleSheet {
     // key is the value of the data-emotion attribute, it's used to identify different sheets
     this.key = options.key
     this.container = options.container
+    this.prepend = options.prepend
     this.before = null
   }
   insert(rule: string) {
@@ -88,7 +91,7 @@ export class StyleSheet {
       let tag = createStyleElement(this)
       let before
       if (this.tags.length === 0) {
-        before = this.before
+        before = this.prepend ? this.container.firstChild : this.before
       } else {
         before = this.tags[this.tags.length - 1].nextSibling
       }
diff --git a/packages/sheet/types/index.d.ts b/packages/sheet/types/index.d.ts
index bda5d570e0..3eac35b53f 100644
--- a/packages/sheet/types/index.d.ts
+++ b/packages/sheet/types/index.d.ts
@@ -6,6 +6,7 @@ export interface Options {
   key: string
   container: HTMLElement
   speedy?: boolean
+  prepend?: boolean
 }
 
 export class StyleSheet {
