diff --git a/.teamcity/hosted/scheduled/build/TeamCityDockerImagesScheduledBuild.kts b/.teamcity/hosted/scheduled/build/TeamCityDockerImagesScheduledBuild.kts
new file mode 100644
index 000000000..43e26b152
--- /dev/null
+++ b/.teamcity/hosted/scheduled/build/TeamCityDockerImagesScheduledBuild.kts
@@ -0,0 +1,43 @@
+package hosted.scheduled.build
+
+import jetbrains.buildServer.configs.kotlin.v2019_2.*
+import jetbrains.buildServer.configs.kotlin.v2019_2.triggers.schedule
+
+/**
+ * Scheduled Composite Build of TeamCity Docker Images for each of supported platforms.
+ * Purpose: ensure that all dependencies within Docker Images are up-to-date.
+ */
+object TeamCityDockerImagesScheduledBuild : BuildType({
+    name = "TeamCity Docker Images - Automated Scheduled Build"
+    description = "Regular automated build of TeamCity Docker Images"
+
+    type = Type.COMPOSITE
+
+    vcs {
+        showDependenciesChanges = true
+    }
+
+    triggers {
+        schedule {
+            id = "TRIGGER_TC_DOCKER_IMAGES_NIGHTLY"
+            schedulingPolicy = daily {
+                hour = 0
+                minute = 15
+            }
+            branchFilter = "+:<default>"
+            withPendingChangesOnly = false
+        }
+    }
+
+    dependencies {
+        arrayOf(
+            TeamCityScheduledImageBuildWindows.TeamCityScheduledImageBuildWindows,
+            TeamCityScheduledImageBuildLinux.TeamCityScheduledImageBuildLinux
+        ).forEach {
+            snapshot(it) {
+                onDependencyFailure = FailureAction.ADD_PROBLEM
+                onDependencyCancel = FailureAction.CANCEL
+            }
+        }
+    }
+})
diff --git a/.teamcity/hosted/scheduled/build/TeamCityScheduledImageBuildLinux.kts b/.teamcity/hosted/scheduled/build/TeamCityScheduledImageBuildLinux.kts
new file mode 100644
index 000000000..b6fae41db
--- /dev/null
+++ b/.teamcity/hosted/scheduled/build/TeamCityScheduledImageBuildLinux.kts
@@ -0,0 +1,51 @@
+package hosted.scheduled.build
+
+import common.TeamCityDockerImagesRepo.TeamCityDockerImagesRepo
+import jetbrains.buildServer.configs.kotlin.v2019_2.BuildType
+import jetbrains.buildServer.configs.kotlin.v2019_2.buildSteps.DockerCommandStep
+import jetbrains.buildServer.configs.kotlin.v2019_2.buildSteps.dockerCommand
+
+
+/**
+ * Scheduled build of TeamCity Docker Images for Linux.
+ */
+object TeamCityScheduledImageBuildLinux : BuildType({
+    name = "TeamCity Docker Images - Automated Scheduled Build - Linux"
+
+    vcs {
+        root(TeamCityDockerImagesRepo)
+    }
+
+    // <image name> - <dockerfile path>
+    val targetImages: HashMap<String, String> = hashMapOf(
+        // Ubuntu 20.04
+        "teamcity-server-linux-20-04" to "context/generated/linux/Server/Ubuntu/20.04/Dockerfile",
+        "teamcity-minimal-agent-linux-20-04" to "context/generated/linux/MinimalAgent/Ubuntu/20.04/Dockerfile",
+        "teamcity-agent-linux-20-04" to "context/generated/linux/Agent/Ubuntu/20.04/Dockerfile",
+        "teamcity-agent-linux-sudo-20-04" to "context/generated/linux/Agent/Ubuntu/20.04-sudo/Dockerfile",
+        // -- ARM images are commented out since TeamCity, currently, does not support it
+        // "teamcity-agent-linux-arm64-20-04" to "context/generated/linux/Agent/UbuntuARM/20.04/Dockerfile",
+        // "teamcity-agent-linux-arm64-sudo-20-04" to "context/generated/linux/Agent/UbuntuARM/20.04-sudo/Dockerfile",
+    )
+
+    steps {
+        targetImages.forEach { (imageName, dockerfilePath) ->
+            dockerCommand {
+                name = "build $imageName"
+                commandType = build {
+                    source = file {
+                        path = dockerfilePath
+                    }
+                    platform = DockerCommandStep.ImagePlatform.Linux
+                    contextDir = "context"
+                    namesAndTags = "${imageName}:%dockerImage.teamcity.buildNumber%"
+                }
+            }
+        }
+    }
+
+    requirements {
+        contains("docker.server.osType", "linux")
+        contains("system.agent.name", "docker")
+    }
+})
diff --git a/.teamcity/hosted/scheduled/build/TeamCityScheduledImageBuildWindows.kts b/.teamcity/hosted/scheduled/build/TeamCityScheduledImageBuildWindows.kts
new file mode 100644
index 000000000..47d1a1658
--- /dev/null
+++ b/.teamcity/hosted/scheduled/build/TeamCityScheduledImageBuildWindows.kts
@@ -0,0 +1,53 @@
+package hosted.scheduled.build
+
+import common.TeamCityDockerImagesRepo.TeamCityDockerImagesRepo
+import jetbrains.buildServer.configs.kotlin.v2019_2.BuildType
+import jetbrains.buildServer.configs.kotlin.v2019_2.buildSteps.DockerCommandStep
+import jetbrains.buildServer.configs.kotlin.v2019_2.buildSteps.dockerCommand
+
+/**
+ * Scheduled build of TeamCity Docker Images for Windows.
+ */
+object TeamCityScheduledImageBuildWindows : BuildType({
+    name = "TeamCity Docker Images - Automated Scheduled Build - Windows"
+
+    vcs {
+        root(TeamCityDockerImagesRepo)
+    }
+
+    // <image name> - <dockerfile path>
+    val targetImages: HashMap<String, String> = hashMapOf(
+        // Windows 1809
+        "teamcity-server-nanoserver-1809" to "context/generated/windows/Server/nanoserver/1809/Dockerfile",
+        "teamcity-minimal-agent-nanoserver-1809" to "context/generated/windows/MinimalAgent/nanoserver/1809/Dockerfile",
+        "teamcity-agent-windowsservercore-1809" to "context/generated/windows/Agent/windowsservercore/1809/Dockerfile",
+        "teamcity-agent-nanoserver-1809" to "context/generated/windows/Agent/nanoserver/1809/Dockerfile",
+
+        // Windows 20.04
+        "teamcity-server-nanoserver-2004" to "context/generated/windows/Server/nanoserver/2004/Dockerfile",
+        "teamcity-minimal-agent-nanoserver-2004" to "context/generated/windows/MinimalAgent/nanoserver/2004/Dockerfile",
+        "teamcity-agent-windowsservercore-2004" to "context/generated/windows/Agent/windowsservercore/2004/Dockerfile",
+        "teamcity-agent-nanoserver-2004" to "context/generated/windows/Agent/nanoserver/2004/Dockerfile",
+    )
+
+    steps {
+        targetImages.forEach { (imageName, dockerfilePath) ->
+            dockerCommand {
+                name = "build $imageName"
+                commandType = build {
+                    source = file {
+                        path = dockerfilePath
+                    }
+                    platform = DockerCommandStep.ImagePlatform.Windows;
+                    contextDir = "context"
+                    namesAndTags = "${imageName}:%dockerImage.teamcity.buildNumber%"
+                }
+            }
+        }
+    }
+
+    requirements {
+        contains("docker.server.osType", "windows")
+        contains("system.agent.name", "docker")
+    }
+})
diff --git a/.teamcity/settings.kts b/.teamcity/settings.kts
index a06452e61..74c2c99c5 100644
--- a/.teamcity/settings.kts
+++ b/.teamcity/settings.kts
@@ -1,7 +1,9 @@
+import Settings.RootProject.buildTypes
 import jetbrains.buildServer.configs.kotlin.v2019_2.*
 import common.TeamCityDockerImagesRepo.TeamCityDockerImagesRepo
 import hosted.*
 import generated.*
+import hosted.scheduled.build.TeamCityDockerImagesScheduledBuild
 
 version = "2019.2"
 
@@ -10,6 +12,7 @@ object RootProject : Project({
     subProject(LocalProject.LocalProject)
     subProject(HubProject.HubProject)
     buildType(BuildAndPushHosted.BuildAndPushHosted)
+    buildType(TeamCityDockerImagesScheduledBuild.TeamCityDockerImagesScheduledBuild)
     params {
         param("dockerImage.teamcity.buildNumber", "%dep.TC_Trunk_BuildDistDocker.build.number%")
         param("teamcity.ui.settings.readOnly", "false")