diff --git a/internal/gatewayapi/testdata/httproute-with-backendref-add-multiple-filters.in.yaml b/internal/gatewayapi/testdata/httproute-with-backendref-add-multiple-filters.in.yaml
index e1ed619de393..4eb7e6f739c6 100644
--- a/internal/gatewayapi/testdata/httproute-with-backendref-add-multiple-filters.in.yaml
+++ b/internal/gatewayapi/testdata/httproute-with-backendref-add-multiple-filters.in.yaml
@@ -30,7 +30,7 @@ httpRoutes:
           backendRefs:
             - name: service-1
               port: 8080
-              weight: 1
+              weight: 8
               filters:
                 - type: RequestHeaderModifier
                   requestHeaderModifier:
@@ -39,16 +39,19 @@ httpRoutes:
                         value: "some-value"
                       - name: "add-header-2"
                         value: "some-value"
-                - type: RequestHeaderModifier
-                  requestHeaderModifier:
-                    add:
-                      - name: "add-header-1"
-                        value: "some-value"
-                      - name: "add-header-3"
-                        value: "some-value"
             - name: service-2
               port: 8080
               weight: 2
+        - matches:
+          - path:
+              value: "/foo"
+          backendRefs:
             - name: service-3
               port: 8080
-              weight: 3
+              weight: 1
+              filters:
+                - type: RequestHeaderModifier
+                  requestHeaderModifier:
+                    set:
+                      - name: "add-header-3"
+                        value: "some-value"
diff --git a/internal/gatewayapi/testdata/httproute-with-backendref-add-multiple-filters.out.yaml b/internal/gatewayapi/testdata/httproute-with-backendref-add-multiple-filters.out.yaml
index 7976ef4c8c48..5971006c8503 100755
--- a/internal/gatewayapi/testdata/httproute-with-backendref-add-multiple-filters.out.yaml
+++ b/internal/gatewayapi/testdata/httproute-with-backendref-add-multiple-filters.out.yaml
@@ -60,26 +60,30 @@ httpRoutes:
             - name: add-header-2
               value: some-value
           type: RequestHeaderModifier
-        - requestHeaderModifier:
-            add:
-            - name: add-header-1
-              value: some-value
-            - name: add-header-3
-              value: some-value
-          type: RequestHeaderModifier
         name: service-1
         port: 8080
-        weight: 1
+        weight: 8
       - name: service-2
         port: 8080
         weight: 2
-      - name: service-3
-        port: 8080
-        weight: 3
       matches:
       - path:
           value: /
       sessionPersistence: null
+    - backendRefs:
+      - filters:
+        - requestHeaderModifier:
+            set:
+            - name: add-header-3
+              value: some-value
+          type: RequestHeaderModifier
+        name: service-3
+        port: 8080
+        weight: 1
+      matches:
+      - path:
+          value: /foo
+      sessionPersistence: null
   status:
     parents:
     - conditions:
@@ -131,9 +135,9 @@ xdsIR:
       routes:
       - backendWeights:
           invalid: 0
-          valid: 6
+          valid: 1
         destination:
-          name: httproute/default/httproute-1/rule/0
+          name: httproute/default/httproute-1/rule/1
           settings:
           - addressType: IP
             endpoints:
@@ -141,31 +145,45 @@ xdsIR:
               port: 8080
             filters:
               addRequestHeaders:
-              - append: true
-                name: add-header-1
-                value: some-value
-              - append: true
-                name: add-header-2
-                value: some-value
-              - append: true
+              - append: false
                 name: add-header-3
                 value: some-value
             protocol: HTTP
             weight: 1
+        hostname: '*'
+        isHTTP2: false
+        name: httproute/default/httproute-1/rule/1/match/0/*
+        pathMatch:
+          distinct: false
+          name: ""
+          prefix: /foo
+      - backendWeights:
+          invalid: 0
+          valid: 10
+        destination:
+          name: httproute/default/httproute-1/rule/0
+          settings:
           - addressType: IP
             endpoints:
             - host: 7.7.7.7
               port: 8080
-            filters: {}
+            filters:
+              addRequestHeaders:
+              - append: true
+                name: add-header-1
+                value: some-value
+              - append: true
+                name: add-header-2
+                value: some-value
             protocol: HTTP
-            weight: 2
+            weight: 8
           - addressType: IP
             endpoints:
             - host: 7.7.7.7
               port: 8080
             filters: {}
             protocol: HTTP
-            weight: 3
+            weight: 2
         hostname: '*'
         isHTTP2: false
         name: httproute/default/httproute-1/rule/0/match/0/*
diff --git a/internal/xds/translator/route.go b/internal/xds/translator/route.go
index 3837f0f5a822..bbdbf6b4f74d 100644
--- a/internal/xds/translator/route.go
+++ b/internal/xds/translator/route.go
@@ -72,7 +72,7 @@ func buildXdsRoute(httpRoute *ir.HTTPRoute) (*routev3.Route, error) {
 		router.Action = &routev3.Route_Route{Route: routeAction}
 	default:
 		var routeAction *routev3.RouteAction
-		if httpRoute.BackendWeights.Invalid != 0 || httpRoute.BackendWeights.Valid > 1 {
+		if hasFiltersInSettings(httpRoute.Destination.Settings) || httpRoute.BackendWeights.Invalid != 0 {
 			// If there are backend weights stored then a weighted cluster is required for the route
 			routeAction = buildXdsWeightedRouteAction(httpRoute)
 		} else {
@@ -272,8 +272,8 @@ func buildXdsWeightedRouteAction(httpRoute *ir.HTTPRoute) *routev3.RouteAction {
 				validCluster.ResponseHeadersToRemove = append(validCluster.ResponseHeadersToRemove, destinationSetting.Filters.RemoveResponseHeaders...)
 			}
 		}
+		weightedClusters = append(weightedClusters, validCluster)
 	}
-	weightedClusters = append(weightedClusters, validCluster)
 
 	return &routev3.RouteAction{
 		// Intentionally route to a non-existent cluster and return a 500 error when it is not found
@@ -597,3 +597,13 @@ func buildRetryOn(triggers []ir.TriggerEnum) (string, error) {
 
 	return b.String(), nil
 }
+
+func hasFiltersInSettings(settings []*ir.DestinationSetting) bool {
+	for _, setting := range settings {
+		filters := setting.Filters
+		if filters != nil {
+			return true
+		}
+	}
+	return false
+}
diff --git a/internal/xds/translator/testdata/in/xds-ir/http-route-weighted-backend-with-filters.yaml b/internal/xds/translator/testdata/in/xds-ir/http-route-weighted-backend-with-filters.yaml
index 940ba1eb0bc4..4dcc8aae5ce1 100644
--- a/internal/xds/translator/testdata/in/xds-ir/http-route-weighted-backend-with-filters.yaml
+++ b/internal/xds/translator/testdata/in/xds-ir/http-route-weighted-backend-with-filters.yaml
@@ -1,45 +1,62 @@
 http:
-- name: "first-listener"
-  address: "0.0.0.0"
-  port: 10080
-  hostnames:
-  - "*"
-  path:
-    mergeSlashes: true
-    escapedSlashesAction: UnescapeAndRedirect
-  routes:
-  - name: "first-route"
-    backendWeights:
-      invalid: 0
-      valid: 20
-    hostname: "*"
-    destination:
-      name: "first-route-dest"
-      settings:
-      - endpoints:
-        - host: "1.1.1.1"
-          port: 50001
-        weight: 20
-        filters:
-          addRequestHeaders:
-          - append: true
-            name: add-header-1
-            value: some-value
-          - append: true
-            name: add-header-2
-            value: some-value
-          - append: true
-            name: add-header-3
-            value: some-value
-      - endpoints:
-        - host: "2.2.2.2"
-          port: 50002
-        weight: 40
-      - endpoints:
-        - host: "3.3.3.3"
-          port: 50003
-        weight: 20
-      - endpoints:
-        - host: "4.4.4.4"
-          port: 50004
-        weight: 20
+  - name: "first-listener"
+    address: "0.0.0.0"
+    hostnames:
+      - '*'
+    path:
+      escapedSlashesAction: UnescapeAndRedirect
+      mergeSlashes: true
+    port: 10080
+    routes:
+      - backendWeights:
+          invalid: 0
+          valid: 1
+        destination:
+          name: "first-route-dest"
+          settings:
+            - addressType: IP
+              endpoints:
+                - host: 1.1.1.1
+                  port: 8080
+              filters:
+                addRequestHeaders:
+                  - append: false
+                    name: add-header-3
+                    value: some-value
+              protocol: HTTP
+              weight: 1
+        hostname: '*'
+        name: "first-route"
+        pathMatch:
+          prefix: /foo
+      - backendWeights:
+          invalid: 0
+          valid: 10
+        destination:
+          name: "second-route-dest"
+          settings:
+          - addressType: IP
+            endpoints:
+            - host: 2.2.2.2
+              port: 8080
+            filters:
+              addRequestHeaders:
+              - append: true
+                name: add-header-1
+                value: some-value
+              - append: true
+                name: add-header-2
+                value: some-value
+            protocol: HTTP
+            weight: 8
+          - addressType: IP
+            endpoints:
+            - host: 3.3.3.3
+              port: 8080
+            filters: {}
+            protocol: HTTP
+            weight: 2
+        hostname: '*'
+        name: "second-route"
+        pathMatch:
+          prefix: /
diff --git a/internal/xds/translator/testdata/out/xds-ir/http-route-weighted-backend-with-filters.clusters.yaml b/internal/xds/translator/testdata/out/xds-ir/http-route-weighted-backend-with-filters.clusters.yaml
index d53a7a1b2ce5..d65e267ad7de 100644
--- a/internal/xds/translator/testdata/out/xds-ir/http-route-weighted-backend-with-filters.clusters.yaml
+++ b/internal/xds/translator/testdata/out/xds-ir/http-route-weighted-backend-with-filters.clusters.yaml
@@ -15,3 +15,20 @@
   outlierDetection: {}
   perConnectionBufferLimitBytes: 32768
   type: EDS
+- circuitBreakers:
+    thresholds:
+    - maxRetries: 1024
+  commonLbConfig:
+    localityWeightedLbConfig: {}
+  connectTimeout: 10s
+  dnsLookupFamily: V4_ONLY
+  edsClusterConfig:
+    edsConfig:
+      ads: {}
+      resourceApiVersion: V3
+    serviceName: second-route-dest
+  lbPolicy: LEAST_REQUEST
+  name: second-route-dest
+  outlierDetection: {}
+  perConnectionBufferLimitBytes: 32768
+  type: EDS
diff --git a/internal/xds/translator/testdata/out/xds-ir/http-route-weighted-backend-with-filters.endpoints.yaml b/internal/xds/translator/testdata/out/xds-ir/http-route-weighted-backend-with-filters.endpoints.yaml
index f5633bd158e3..261bcf04f941 100644
--- a/internal/xds/translator/testdata/out/xds-ir/http-route-weighted-backend-with-filters.endpoints.yaml
+++ b/internal/xds/translator/testdata/out/xds-ir/http-route-weighted-backend-with-filters.endpoints.yaml
@@ -5,38 +5,30 @@
         address:
           socketAddress:
             address: 1.1.1.1
-            portValue: 50001
+            portValue: 8080
       loadBalancingWeight: 1
-    loadBalancingWeight: 20
+    loadBalancingWeight: 1
     locality:
       region: first-route-dest/backend/0
+- clusterName: second-route-dest
+  endpoints:
   - lbEndpoints:
     - endpoint:
         address:
           socketAddress:
             address: 2.2.2.2
-            portValue: 50002
+            portValue: 8080
       loadBalancingWeight: 1
-    loadBalancingWeight: 40
+    loadBalancingWeight: 8
     locality:
-      region: first-route-dest/backend/1
+      region: second-route-dest/backend/0
   - lbEndpoints:
     - endpoint:
         address:
           socketAddress:
             address: 3.3.3.3
-            portValue: 50003
-      loadBalancingWeight: 1
-    loadBalancingWeight: 20
-    locality:
-      region: first-route-dest/backend/2
-  - lbEndpoints:
-    - endpoint:
-        address:
-          socketAddress:
-            address: 4.4.4.4
-            portValue: 50004
+            portValue: 8080
       loadBalancingWeight: 1
-    loadBalancingWeight: 20
+    loadBalancingWeight: 2
     locality:
-      region: first-route-dest/backend/3
+      region: second-route-dest/backend/1
diff --git a/internal/xds/translator/testdata/out/xds-ir/http-route-weighted-backend-with-filters.routes.yaml b/internal/xds/translator/testdata/out/xds-ir/http-route-weighted-backend-with-filters.routes.yaml
index 7e08c106f81f..10bba14aedbf 100644
--- a/internal/xds/translator/testdata/out/xds-ir/http-route-weighted-backend-with-filters.routes.yaml
+++ b/internal/xds/translator/testdata/out/xds-ir/http-route-weighted-backend-with-filters.routes.yaml
@@ -6,7 +6,7 @@
     name: first-listener/*
     routes:
     - match:
-        prefix: /
+        pathSeparatedPrefix: /foo
       name: first-route
       route:
         clusterNotFoundResponseCode: INTERNAL_SERVER_ERROR
@@ -15,6 +15,22 @@
         weightedClusters:
           clusters:
           - name: first-route-dest
+            requestHeadersToAdd:
+            - appendAction: OVERWRITE_IF_EXISTS_OR_ADD
+              header:
+                key: add-header-3
+                value: some-value
+            weight: 1
+    - match:
+        prefix: /
+      name: second-route
+      route:
+        clusterNotFoundResponseCode: INTERNAL_SERVER_ERROR
+        upgradeConfigs:
+        - upgradeType: websocket
+        weightedClusters:
+          clusters:
+          - name: second-route-dest
             requestHeadersToAdd:
             - header:
                 key: add-header-1
@@ -22,7 +38,13 @@
             - header:
                 key: add-header-2
                 value: some-value
+            weight: 10
+          - name: second-route-dest
+            requestHeadersToAdd:
             - header:
-                key: add-header-3
+                key: add-header-1
+                value: some-value
+            - header:
+                key: add-header-2
                 value: some-value
-            weight: 20
+            weight: 10