diff --git a/.github/workflows/wiki.yml b/.github/workflows/wiki.yml
index f37031f61e9..1875e6154be 100644
--- a/.github/workflows/wiki.yml
+++ b/.github/workflows/wiki.yml
@@ -1,20 +1,41 @@
 name: Deploy to Wiki
 on:
+  pull_request:
+    paths:
+      - 'wiki/**'
   push:
     branches:
       - develop
     paths:
       - 'wiki/**'
-  # Triggers this workflow when the wiki is changed
+  # Triggers this workflow when the wiki is changed.
   # (see https://docs.github.com/en/actions/using-workflows/events-that-trigger-workflows#gollum).
   gollum:
 
 jobs:
+  table_of_contents_check:
+    # To verify that the wiki's table of contents matches the headers accurately.
+    name: Check Wiki Table of Contents
+    runs-on: ubuntu-20.04
+    steps:
+      - uses: actions/checkout@v2
+
+      - name: Set up Bazel
+        uses: abhinavsingh/setup-bazel@v3
+        with:
+          version: 6.5.0
+
+      - name: Check Wiki Table of Contents
+        id: checkWikiToc
+        run: |
+          bazel run //scripts:wiki_table_of_contents_check -- ${GITHUB_WORKSPACE}
+
   wiki-deploy:
     runs-on: ${{ matrix.os }}
     strategy:
       matrix:
         os: [ubuntu-20.04]
+    if: ${{ github.event_name == 'push' && github.ref == 'refs/heads/develop' }}
     steps:
       - uses: actions/checkout@v3
         with:
diff --git a/scripts/BUILD.bazel b/scripts/BUILD.bazel
index 6ef9a5d6739..9577dfe834b 100644
--- a/scripts/BUILD.bazel
+++ b/scripts/BUILD.bazel
@@ -237,6 +237,15 @@ kt_jvm_binary(
     ],
 )
 
+kt_jvm_binary(
+    name = "wiki_table_of_contents_check",
+    testonly = True,
+    main_class = "org.oppia.android.scripts.wiki.WikiTableOfContentsCheckKt",
+    runtime_deps = [
+        "//scripts/src/java/org/oppia/android/scripts/wiki:wiki_table_of_contents_check_lib",
+    ],
+)
+
 kt_jvm_binary(
     name = "run_coverage",
     testonly = True,
diff --git a/scripts/src/java/org/oppia/android/scripts/wiki/BUILD.bazel b/scripts/src/java/org/oppia/android/scripts/wiki/BUILD.bazel
new file mode 100644
index 00000000000..6898d1b8c21
--- /dev/null
+++ b/scripts/src/java/org/oppia/android/scripts/wiki/BUILD.bazel
@@ -0,0 +1,18 @@
+"""
+Libraries corresponding to scripting tools that help with continuous integration workflows.
+"""
+
+load("@io_bazel_rules_kotlin//kotlin:kotlin.bzl", "kt_jvm_library")
+
+kt_jvm_library(
+    name = "wiki_table_of_contents_check_lib",
+    testonly = True,
+    srcs = [
+        "WikiTableOfContentsCheck.kt",
+    ],
+    visibility = ["//scripts:oppia_script_binary_visibility"],
+    deps = [
+        "//scripts/src/java/org/oppia/android/scripts/common:bazel_client",
+        "//scripts/src/java/org/oppia/android/scripts/common:git_client",
+    ],
+)
diff --git a/scripts/src/java/org/oppia/android/scripts/wiki/WikiTableOfContentsCheck.kt b/scripts/src/java/org/oppia/android/scripts/wiki/WikiTableOfContentsCheck.kt
new file mode 100644
index 00000000000..c634792e7a9
--- /dev/null
+++ b/scripts/src/java/org/oppia/android/scripts/wiki/WikiTableOfContentsCheck.kt
@@ -0,0 +1,98 @@
+package org.oppia.android.scripts.wiki
+
+import java.io.File
+
+/**
+ * Script for ensuring that the table of contents in each wiki page matches with its respective headers.
+ *
+ * Usage:
+ *   bazel run //scripts:wiki_table_of_contents_check -- <path_to_default_working_directory>
+ *
+ * Arguments:
+ * - path_to_default_working_directory: The default working directory on the runner for steps, and the default location of repository.
+ *
+ * Example:
+ *   bazel run //scripts:wiki_table_of_contents_check -- $(pwd)
+ */
+fun main(vararg args: String) {
+  // Path to the repo's wiki.
+  val wikiDirPath = "${args[0]}/wiki/"
+  val wikiDir = File(wikiDirPath)
+
+  // Check if the wiki directory exists.
+  if (wikiDir.exists() && wikiDir.isDirectory) {
+    processWikiDirectory(wikiDir)
+    println("WIKI TABLE OF CONTENTS CHECK PASSED")
+  } else {
+    println("No contents found in the Wiki directory.")
+  }
+}
+
+/**
+ * Checks every file in the wiki repo.
+ *
+ * @param wikiDir the default working directory
+ */
+fun processWikiDirectory(wikiDir: File) {
+  wikiDir.listFiles()?.forEach { file ->
+    checkTableOfContents(file)
+  }
+}
+
+/**
+ * Checks the contents of a single wiki file to ensure the accuracy of the Table of Contents.
+ *
+ * @param file the wiki file to process.
+ */
+fun checkTableOfContents(file: File) {
+  val fileContents = file.readLines()
+  val tocStartIdx = fileContents.indexOfFirst {
+    it.contains(Regex("""##\s+Table\s+of\s+Contents""", RegexOption.IGNORE_CASE))
+  }
+  if (tocStartIdx == -1) {
+    return
+  }
+
+  // Skipping the blank line after the ## Table of Contents
+  val eOfIdx = fileContents.subList(tocStartIdx + 2, fileContents.size).indexOfFirst {
+    it.isBlank()
+  }
+  if (eOfIdx == -1) error("Table of Contents didn't end with a blank line.")
+
+  val tocSpecificLines = fileContents.subList(tocStartIdx, tocStartIdx + eOfIdx + 1)
+
+  for (line in tocSpecificLines) {
+    if (line.trimStart().startsWith("- [") && !line.contains("https://")) {
+      validateTableOfContents(file, line)
+    }
+  }
+}
+
+/**
+ * Validates the accuracy of a Table of Contents entry in a wiki file.
+ *
+ * @param file the wiki file being validated.
+ * @param line the line containing the Table of Contents entry.
+ */
+fun validateTableOfContents(file: File, line: String) {
+  val titleRegex = "\\[(.*?)\\]".toRegex()
+  val title = titleRegex.find(line)?.groupValues?.get(1)?.replace('-', ' ')
+    ?.replace(Regex("[?&./:’'*!,(){}\\[\\]+]"), "")
+    ?.trim()
+
+  val linkRegex = "\\(#(.*?)\\)".toRegex()
+  val link = linkRegex.find(line)?.groupValues?.get(1)?.removePrefix("#")?.replace('-', ' ')
+    ?.replace(Regex("[?&./:’'*!,(){}\\[\\]+]"), "")
+    ?.trim()
+
+  // Checks if the table of content title matches with the header link text.
+  val matches = title.equals(link, ignoreCase = true)
+  if (!matches) {
+    error(
+      "\nWIKI TABLE OF CONTENTS CHECK FAILED" +
+        "\nMismatch of Table of Content with headers in the File: ${file.name}. " +
+        "\nThe Title: '${titleRegex.find(line)?.groupValues?.get(1)}' " +
+        "doesn't match with its corresponding Link: '${linkRegex.find(line)?.groupValues?.get(1)}'."
+    )
+  }
+}
diff --git a/scripts/src/javatests/org/oppia/android/scripts/wiki/BUILD.bazel b/scripts/src/javatests/org/oppia/android/scripts/wiki/BUILD.bazel
new file mode 100644
index 00000000000..953b3f7d8d9
--- /dev/null
+++ b/scripts/src/javatests/org/oppia/android/scripts/wiki/BUILD.bazel
@@ -0,0 +1,16 @@
+"""
+Tests corresponding to wiki-related checks.
+"""
+
+load("@io_bazel_rules_kotlin//kotlin:jvm.bzl", "kt_jvm_test")
+
+kt_jvm_test(
+    name = "WikiTableOfContentsCheckTest",
+    srcs = ["WikiTableOfContentsCheckTest.kt"],
+    deps = [
+        "//scripts/src/java/org/oppia/android/scripts/wiki:wiki_table_of_contents_check_lib",
+        "//testing:assertion_helpers",
+        "//third_party:com_google_truth_truth",
+        "//third_party:org_jetbrains_kotlin_kotlin-test-junit",
+    ],
+)
diff --git a/scripts/src/javatests/org/oppia/android/scripts/wiki/WikiTableOfContentsCheckTest.kt b/scripts/src/javatests/org/oppia/android/scripts/wiki/WikiTableOfContentsCheckTest.kt
new file mode 100644
index 00000000000..8b91a453107
--- /dev/null
+++ b/scripts/src/javatests/org/oppia/android/scripts/wiki/WikiTableOfContentsCheckTest.kt
@@ -0,0 +1,168 @@
+package org.oppia.android.scripts.wiki
+
+import com.google.common.truth.Truth.assertThat
+import org.junit.After
+import org.junit.Before
+import org.junit.Rule
+import org.junit.Test
+import org.junit.rules.TemporaryFolder
+import org.oppia.android.testing.assertThrows
+import java.io.ByteArrayOutputStream
+import java.io.PrintStream
+
+/** Tests for [WikiTableOfContentsCheck]. */
+class WikiTableOfContentsCheckTest {
+  private val outContent: ByteArrayOutputStream = ByteArrayOutputStream()
+  private val originalOut: PrintStream = System.out
+  private val WIKI_TOC_CHECK_PASSED_OUTPUT_INDICATOR = "WIKI TABLE OF CONTENTS CHECK PASSED"
+  private val WIKI_TOC_CHECK_FAILED_OUTPUT_INDICATOR = "WIKI TABLE OF CONTENTS CHECK FAILED"
+
+  @field:[Rule JvmField] val tempFolder = TemporaryFolder()
+
+  @Before
+  fun setUp() {
+    System.setOut(PrintStream(outContent))
+  }
+
+  @After
+  fun tearDown() {
+    System.setOut(originalOut)
+  }
+
+  @Test
+  fun testWikiTOCCheck_noWikiDirExists_printsNoContentFound() {
+    runScript()
+    assertThat(outContent.toString().trim()).isEqualTo("No contents found in the Wiki directory.")
+  }
+
+  @Test
+  fun testWikiTOCCheck_noWikiDirectory_printsNoContentFound() {
+    tempFolder.newFile("wiki")
+    runScript()
+    assertThat(outContent.toString().trim()).isEqualTo("No contents found in the Wiki directory.")
+  }
+
+  @Test
+  fun testWikiTOCCheck_validWikiTOC_checkPass() {
+    tempFolder.newFolder("wiki")
+    val file = tempFolder.newFile("wiki/wiki.md")
+    file.writeText(
+      """
+            ## Table of Contents
+            
+            - [Introduction](#introduction)
+            - [Usage](#usage)
+            
+            ## Introduction
+            Content
+            
+            ## Usage
+            Content
+      """.trimIndent()
+    )
+
+    runScript()
+
+    assertThat(outContent.toString().trim()).contains(WIKI_TOC_CHECK_PASSED_OUTPUT_INDICATOR)
+  }
+
+  @Test
+  fun testWikiTOCCheck_missingWikiTOC_returnsNoTOCFound() {
+    tempFolder.newFolder("wiki")
+    val file = tempFolder.newFile("wiki/wiki.md")
+    file.writeText(
+      """          
+            - [Introduction](#introduction)
+            - [Usage](#usage)
+            
+            ## Introduction
+            Content
+            
+            ## Usage
+            Content
+      """.trimIndent()
+    )
+
+    runScript()
+
+    assertThat(outContent.toString().trim()).contains(WIKI_TOC_CHECK_PASSED_OUTPUT_INDICATOR)
+  }
+
+  @Test
+  fun testWikiTOCCheck_mismatchWikiTOC_checkFail() {
+    tempFolder.newFolder("wiki")
+    val file = tempFolder.newFile("wiki/wiki.md")
+    file.writeText(
+      """   
+            ## Table of Contents
+             
+            - [Introduction](#introductions)
+            - [Usage](#usage)
+            
+            ## Introduction
+            Content
+            
+            ## Usage
+            Content
+      """.trimIndent()
+    )
+
+    val exception = assertThrows<IllegalStateException>() {
+      runScript()
+    }
+
+    assertThat(exception).hasMessageThat().contains(WIKI_TOC_CHECK_FAILED_OUTPUT_INDICATOR)
+  }
+
+  @Test
+  fun testWikiTOCCheck_validWikiTOCWithSeparator_checkPass() {
+    tempFolder.newFolder("wiki")
+    val file = tempFolder.newFile("wiki/wiki.md")
+    file.writeText(
+      """   
+            ## Table of Contents
+             
+            - [Introduction To Wiki](#introduction-to-wiki)
+            - [Usage Wiki-Content](#usage-wiki-content)
+            
+            ## Introduction
+            Content
+            
+            ## Usage
+            Content
+      """.trimIndent()
+    )
+
+    runScript()
+
+    assertThat(outContent.toString().trim()).contains(WIKI_TOC_CHECK_PASSED_OUTPUT_INDICATOR)
+  }
+
+  @Test
+  fun testWikiTOCCheck_validWikiTOCWithSpecialCharacter_checkPass() {
+    tempFolder.newFolder("wiki")
+    val file = tempFolder.newFile("wiki/wiki.md")
+    file.writeText(
+      """   
+            ## Table of Contents
+             
+            - [Introduction](#introduction?)
+            - [Usage?](#usage)
+            
+            ## Introduction
+            Content
+            
+            ## Usage
+            Content
+      """.trimIndent()
+    )
+
+    runScript()
+
+    assertThat(outContent.toString().trim()).contains(WIKI_TOC_CHECK_PASSED_OUTPUT_INDICATOR)
+  }
+
+  private fun runScript() {
+    main(tempFolder.root.absolutePath)
+  }
+}