diff --git a/models/webhook/hooktask.go b/models/webhook/hooktask.go
index 1967ded29..1d19ebd24 100644
--- a/models/webhook/hooktask.go
+++ b/models/webhook/hooktask.go
@@ -175,18 +175,13 @@ func HookTasks(hookID int64, page int) ([]*HookTask, error) {
 // CreateHookTask creates a new hook task,
 // it handles conversion from Payload to PayloadContent.
 func CreateHookTask(t *HookTask) error {
-	return createHookTask(db.GetEngine(db.DefaultContext), t)
-}
-
-func createHookTask(e db.Engine, t *HookTask) error {
 	data, err := t.Payloader.JSONPayload()
 	if err != nil {
 		return err
 	}
 	t.UUID = gouuid.New().String()
 	t.PayloadContent = string(data)
-	_, err = e.Insert(t)
-	return err
+	return db.Insert(db.DefaultContext, t)
 }
 
 // UpdateHookTask updates information of hook task.
@@ -195,6 +190,38 @@ func UpdateHookTask(t *HookTask) error {
 	return err
 }
 
+// ReplayHookTask copies a hook task to get re-delivered
+func ReplayHookTask(hookID int64, uuid string) (*HookTask, error) {
+	var newTask *HookTask
+
+	err := db.WithTx(func(ctx context.Context) error {
+		task := &HookTask{
+			HookID: hookID,
+			UUID:   uuid,
+		}
+		has, err := db.GetByBean(ctx, task)
+		if err != nil {
+			return err
+		} else if !has {
+			return ErrHookTaskNotExist{
+				HookID: hookID,
+				UUID:   uuid,
+			}
+		}
+
+		newTask = &HookTask{
+			UUID:           gouuid.New().String(),
+			RepoID:         task.RepoID,
+			HookID:         task.HookID,
+			PayloadContent: task.PayloadContent,
+			EventType:      task.EventType,
+		}
+		return db.Insert(ctx, newTask)
+	})
+
+	return newTask, err
+}
+
 // FindUndeliveredHookTasks represents find the undelivered hook tasks
 func FindUndeliveredHookTasks() ([]*HookTask, error) {
 	tasks := make([]*HookTask, 0, 10)
diff --git a/models/webhook/webhook.go b/models/webhook/webhook.go
index d01f548ee..21c01d928 100644
--- a/models/webhook/webhook.go
+++ b/models/webhook/webhook.go
@@ -41,6 +41,22 @@ func (err ErrWebhookNotExist) Error() string {
 	return fmt.Sprintf("webhook does not exist [id: %d]", err.ID)
 }
 
+// ErrHookTaskNotExist represents a "HookTaskNotExist" kind of error.
+type ErrHookTaskNotExist struct {
+	HookID int64
+	UUID   string
+}
+
+// IsErrWebhookNotExist checks if an error is a ErrWebhookNotExist.
+func IsErrHookTaskNotExist(err error) bool {
+	_, ok := err.(ErrHookTaskNotExist)
+	return ok
+}
+
+func (err ErrHookTaskNotExist) Error() string {
+	return fmt.Sprintf("hook task does not exist [hook: %d, uuid: %s]", err.HookID, err.UUID)
+}
+
 // HookContentType is the content type of a web hook
 type HookContentType int
 
diff --git a/options/locale/locale_en-US.ini b/options/locale/locale_en-US.ini
index 7a3dbd50a..3d60df5d6 100644
--- a/options/locale/locale_en-US.ini
+++ b/options/locale/locale_en-US.ini
@@ -1831,12 +1831,13 @@ settings.webhook_deletion_desc = Removing a webhook deletes its settings and del
 settings.webhook_deletion_success = The webhook has been removed.
 settings.webhook.test_delivery = Test Delivery
 settings.webhook.test_delivery_desc = Test this webhook with a fake event.
-settings.webhook.test_delivery_success = A fake event has been added to the delivery queue. It may take few seconds before it shows up in the delivery history.
 settings.webhook.request = Request
 settings.webhook.response = Response
 settings.webhook.headers = Headers
 settings.webhook.payload = Content
 settings.webhook.body = Body
+settings.webhook.replay.description = Replay this webhook.
+settings.webhook.delivery.success = An event has been added to the delivery queue. It may take few seconds before it shows up in the delivery history.
 settings.githooks_desc = "Git Hooks are powered by Git itself. You can edit hook files below to set up custom operations."
 settings.githook_edit_desc = If the hook is inactive, sample content will be presented. Leaving content to an empty value will disable this hook.
 settings.githook_name = Hook Name
diff --git a/routers/web/repo/webhook.go b/routers/web/repo/webhook.go
index 47d841367..2ec2e8911 100644
--- a/routers/web/repo/webhook.go
+++ b/routers/web/repo/webhook.go
@@ -1189,11 +1189,33 @@ func TestWebhook(ctx *context.Context) {
 		ctx.Flash.Error("PrepareWebhook: " + err.Error())
 		ctx.Status(500)
 	} else {
-		ctx.Flash.Info(ctx.Tr("repo.settings.webhook.test_delivery_success"))
+		ctx.Flash.Info(ctx.Tr("repo.settings.webhook.delivery.success"))
 		ctx.Status(200)
 	}
 }
 
+// ReplayWebhook replays a webhook
+func ReplayWebhook(ctx *context.Context) {
+	hookTaskUUID := ctx.Params(":uuid")
+
+	orCtx, w := checkWebhook(ctx)
+	if ctx.Written() {
+		return
+	}
+
+	if err := webhook_service.ReplayHookTask(w, hookTaskUUID); err != nil {
+		if webhook.IsErrHookTaskNotExist(err) {
+			ctx.NotFound("ReplayHookTask", nil)
+		} else {
+			ctx.ServerError("ReplayHookTask", err)
+		}
+		return
+	}
+
+	ctx.Flash.Success(ctx.Tr("repo.settings.webhook.delivery.success"))
+	ctx.Redirect(fmt.Sprintf("%s/%d", orCtx.Link, w.ID))
+}
+
 // DeleteWebhook delete a webhook
 func DeleteWebhook(ctx *context.Context) {
 	if err := webhook.DeleteWebhookByRepoID(ctx.Repo.Repository.ID, ctx.FormInt64("id")); err != nil {
diff --git a/routers/web/web.go b/routers/web/web.go
index e35ccb5aa..8abdf7c61 100644
--- a/routers/web/web.go
+++ b/routers/web/web.go
@@ -435,7 +435,10 @@ func RegisterRoutes(m *web.Route) {
 		m.Group("/hooks", func() {
 			m.Get("", admin.DefaultOrSystemWebhooks)
 			m.Post("/delete", admin.DeleteDefaultOrSystemWebhook)
-			m.Get("/{id}", repo.WebHooksEdit)
+			m.Group("/{id}", func() {
+				m.Get("", repo.WebHooksEdit)
+				m.Post("/replay/{uuid}", repo.ReplayWebhook)
+			})
 			m.Post("/gitea/{id}", bindIgnErr(forms.NewWebhookForm{}), repo.WebHooksEditPost)
 			m.Post("/gogs/{id}", bindIgnErr(forms.NewGogshookForm{}), repo.GogsHooksEditPost)
 			m.Post("/slack/{id}", bindIgnErr(forms.NewSlackHookForm{}), repo.SlackHooksEditPost)
@@ -559,7 +562,10 @@ func RegisterRoutes(m *web.Route) {
 					m.Post("/msteams/new", bindIgnErr(forms.NewMSTeamsHookForm{}), repo.MSTeamsHooksNewPost)
 					m.Post("/feishu/new", bindIgnErr(forms.NewFeishuHookForm{}), repo.FeishuHooksNewPost)
 					m.Post("/wechatwork/new", bindIgnErr(forms.NewWechatWorkHookForm{}), repo.WechatworkHooksNewPost)
-					m.Get("/{id}", repo.WebHooksEdit)
+					m.Group("/{id}", func() {
+						m.Get("", repo.WebHooksEdit)
+						m.Post("/replay/{uuid}", repo.ReplayWebhook)
+					})
 					m.Post("/gitea/{id}", bindIgnErr(forms.NewWebhookForm{}), repo.WebHooksEditPost)
 					m.Post("/gogs/{id}", bindIgnErr(forms.NewGogshookForm{}), repo.GogsHooksEditPost)
 					m.Post("/slack/{id}", bindIgnErr(forms.NewSlackHookForm{}), repo.SlackHooksEditPost)
@@ -653,8 +659,11 @@ func RegisterRoutes(m *web.Route) {
 				m.Post("/msteams/new", bindIgnErr(forms.NewMSTeamsHookForm{}), repo.MSTeamsHooksNewPost)
 				m.Post("/feishu/new", bindIgnErr(forms.NewFeishuHookForm{}), repo.FeishuHooksNewPost)
 				m.Post("/wechatwork/new", bindIgnErr(forms.NewWechatWorkHookForm{}), repo.WechatworkHooksNewPost)
-				m.Get("/{id}", repo.WebHooksEdit)
-				m.Post("/{id}/test", repo.TestWebhook)
+				m.Group("/{id}", func() {
+					m.Get("", repo.WebHooksEdit)
+					m.Post("/test", repo.TestWebhook)
+					m.Post("/replay/{uuid}", repo.ReplayWebhook)
+				})
 				m.Post("/gitea/{id}", bindIgnErr(forms.NewWebhookForm{}), repo.WebHooksEditPost)
 				m.Post("/gogs/{id}", bindIgnErr(forms.NewGogshookForm{}), repo.GogsHooksEditPost)
 				m.Post("/slack/{id}", bindIgnErr(forms.NewSlackHookForm{}), repo.SlackHooksEditPost)
diff --git a/services/webhook/webhook.go b/services/webhook/webhook.go
index 9356f4ee1..f284a20c3 100644
--- a/services/webhook/webhook.go
+++ b/services/webhook/webhook.go
@@ -229,3 +229,15 @@ func prepareWebhooks(repo *repo_model.Repository, event webhook_model.HookEventT
 	}
 	return nil
 }
+
+// ReplayHookTask replays a webhook task
+func ReplayHookTask(w *webhook_model.Webhook, uuid string) error {
+	t, err := webhook_model.ReplayHookTask(w.ID, uuid)
+	if err != nil {
+		return err
+	}
+
+	go hookQueue.Add(t.RepoID)
+
+	return nil
+}
diff --git a/templates/admin/hook_new.tmpl b/templates/admin/hook_new.tmpl
index 4710498b2..2cd3fc826 100644
--- a/templates/admin/hook_new.tmpl
+++ b/templates/admin/hook_new.tmpl
@@ -1,5 +1,5 @@
 {{template "base/head" .}}
-<div class="page-content admin new webhook">
+<div class="page-content admin settings new webhook">
 	{{template "admin/navbar" .}}
 	<div class="ui container">
 		{{template "base/alert" .}}
diff --git a/templates/repo/settings/webhook/history.tmpl b/templates/repo/settings/webhook/history.tmpl
index 8823d6c1d..a719e4453 100644
--- a/templates/repo/settings/webhook/history.tmpl
+++ b/templates/repo/settings/webhook/history.tmpl
@@ -40,6 +40,14 @@
 									<span class="ui label">N/A</span>
 								{{end}}
 							</a>
+							{{if or $.Permission.IsAdmin $.IsOrganizationOwner $.PageIsAdmin}}
+							<div class="right menu">
+								<form class="item" action="{{$.Link}}/replay/{{.UUID}}" method="post">
+									{{$.CsrfTokenHtml}}
+									<button class="ui tiny button tooltip" data-content="{{$.i18n.Tr "repo.settings.webhook.replay.description"}}" data-variation="inverted tiny">{{svg "octicon-sync"}}</button>
+								</form>
+							</div>
+							{{end}}
 						</div>
 						<div class="ui bottom attached tab segment active" data-tab="request-{{.ID}}">
 							{{if .RequestInfo}}