diff --git a/CHANGELOG.md b/CHANGELOG.md
index 1d7b0f38a651..8af96b47e1cd 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -25,6 +25,7 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 - Create tailwind.config.cjs file in ESM package when running init ([#8363](https://github.com/tailwindlabs/tailwindcss/pull/8363))
 - Fix `matchVariants` that use at-rules and placeholders ([#8392](https://github.com/tailwindlabs/tailwindcss/pull/8392))
 - Improve types of the `tailwindcss/plugin` ([#8400](https://github.com/tailwindlabs/tailwindcss/pull/8400))
+- Allow returning parallel variants from `addVariant` or `matchVariant` callback functions ([#8455](https://github.com/tailwindlabs/tailwindcss/pull/8455))
 
 ### Changed
 
diff --git a/jest/customMatchers.js b/jest/customMatchers.js
index 3f1ea2d83d50..385faf7bdda5 100644
--- a/jest/customMatchers.js
+++ b/jest/customMatchers.js
@@ -100,7 +100,7 @@ expect.extend({
 expect.extend({
   // Compare two CSS strings with all whitespace removed
   // This is probably naive but it's fast and works well enough.
-  toMatchFormattedCss(received, argument) {
+  toMatchFormattedCss(received = '', argument = '') {
     function format(input) {
       return prettier.format(input.replace(/\n/g, ''), {
         parser: 'css',
diff --git a/src/lib/generateRules.js b/src/lib/generateRules.js
index d1f216dd4d9b..c5f82d8c391c 100644
--- a/src/lib/generateRules.js
+++ b/src/lib/generateRules.js
@@ -152,7 +152,7 @@ function applyVariant(variant, matches, context) {
   }
 
   if (context.variantMap.has(variant)) {
-    let variantFunctionTuples = context.variantMap.get(variant)
+    let variantFunctionTuples = context.variantMap.get(variant).slice()
     let result = []
 
     for (let [meta, rule] of matches) {
@@ -216,6 +216,26 @@ function applyVariant(variant, matches, context) {
           args,
         })
 
+        // It can happen that a list of format strings is returned from within the function. In that
+        // case, we have to process them as well. We can use the existing `variantSort`.
+        if (Array.isArray(ruleWithVariant)) {
+          for (let [idx, variantFunction] of ruleWithVariant.entries()) {
+            // This is a little bit scary since we are pushing to an array of items that we are
+            // currently looping over. However, you can also think of it like a processing queue
+            // where you keep handling jobs until everything is done and each job can queue more
+            // jobs if needed.
+            variantFunctionTuples.push([
+              // TODO: This could have potential bugs if we shift the sort order from variant A far
+              // enough into the sort space of variant B. The chances are low, but if this happens
+              // then this might be the place too look at. One potential solution to this problem is
+              // reserving additional X places for these 'unknown' variants in between.
+              variantSort | BigInt(idx << ruleWithVariant.length),
+              variantFunction,
+            ])
+          }
+          continue
+        }
+
         if (typeof ruleWithVariant === 'string') {
           collectedFormats.push(ruleWithVariant)
         }
diff --git a/src/lib/setupContextUtils.js b/src/lib/setupContextUtils.js
index 5f0a3203ede7..004b8f9756cb 100644
--- a/src/lib/setupContextUtils.js
+++ b/src/lib/setupContextUtils.js
@@ -463,6 +463,10 @@ function buildPluginApi(tailwindConfig, context, { variantList, variantMap, offs
               )
             }
 
+            if (Array.isArray(result)) {
+              return result.map((variant) => parseVariant(variant))
+            }
+
             // result may be undefined with legacy variants that use APIs like `modifySelectors`
             return result && parseVariant(result)(api)
           }
diff --git a/tests/match-variants.test.js b/tests/match-variants.test.js
index 1f0252ce8178..528a63e9ff94 100644
--- a/tests/match-variants.test.js
+++ b/tests/match-variants.test.js
@@ -206,3 +206,41 @@ test('matched variant values maintain the sort order they are registered in', ()
     `)
   })
 })
+
+test('matchVariant can return an array of format strings from the function', () => {
+  let config = {
+    content: [
+      {
+        raw: html`<div class="test-[a,b,c]:underline"></div>`,
+      },
+    ],
+    corePlugins: { preflight: false },
+    plugins: [
+      ({ matchVariant }) => {
+        matchVariant({
+          test: (selector) => selector.split(',').map((selector) => `&.${selector} > *`),
+        })
+      },
+    ],
+  }
+
+  let input = css`
+    @tailwind utilities;
+  `
+
+  return run(input, config).then((result) => {
+    expect(result.css).toMatchFormattedCss(css`
+      .test-\[a\2c b\2c c\]\:underline.a > * {
+        text-decoration-line: underline;
+      }
+
+      .test-\[a\2c b\2c c\]\:underline.b > * {
+        text-decoration-line: underline;
+      }
+
+      .test-\[a\2c b\2c c\]\:underline.c > * {
+        text-decoration-line: underline;
+      }
+    `)
+  })
+})
diff --git a/tests/parallel-variants.test.js b/tests/parallel-variants.test.js
index 94cb1bc13f90..f1be86832884 100644
--- a/tests/parallel-variants.test.js
+++ b/tests/parallel-variants.test.js
@@ -42,3 +42,46 @@ test('basic parallel variants', async () => {
     `)
   })
 })
+
+test('parallel variants can be generated using a function that returns parallel variants', async () => {
+  let config = {
+    content: [
+      {
+        raw: html`<div
+          class="hover:test:font-black test:font-bold test:font-medium font-normal"
+        ></div>`,
+      },
+    ],
+    plugins: [
+      function test({ addVariant }) {
+        addVariant('test', () => ['& *::test', '&::test'])
+      },
+    ],
+  }
+
+  return run('@tailwind utilities', config).then((result) => {
+    expect(result.css).toMatchFormattedCss(css`
+      .font-normal {
+        font-weight: 400;
+      }
+      .test\:font-bold *::test {
+        font-weight: 700;
+      }
+      .test\:font-medium *::test {
+        font-weight: 500;
+      }
+      .test\:font-bold::test {
+        font-weight: 700;
+      }
+      .test\:font-medium::test {
+        font-weight: 500;
+      }
+      .hover\:test\:font-black *:hover::test {
+        font-weight: 900;
+      }
+      .hover\:test\:font-black:hover::test {
+        font-weight: 900;
+      }
+    `)
+  })
+})