diff --git a/packages/react-router/src/link.tsx b/packages/react-router/src/link.tsx
index 9ec0835c0b..c90be7f361 100644
--- a/packages/react-router/src/link.tsx
+++ b/packages/react-router/src/link.tsx
@@ -71,7 +71,14 @@ export type Split<S, TIncludeTrailingSlash = true> = S extends unknown
   : never
 
 export type ParsePathParams<T extends string> = keyof {
-  [K in Trim<Split<T>[number], '_'> as K extends `$${infer L}` ? L : never]: K
+  [K in Trim<
+    Split<T>[number],
+    '_'
+  > as K extends `${string}$${infer L}$${string}`
+    ? L
+    : K extends `${string}$${infer L}`
+    ? L
+    : never]: K
 }
 
 export type Join<T, Delimiter extends string = '/'> = T extends []
diff --git a/packages/react-router/src/path.ts b/packages/react-router/src/path.ts
index fd4450ef4a..77e6cde72b 100644
--- a/packages/react-router/src/path.ts
+++ b/packages/react-router/src/path.ts
@@ -97,7 +97,7 @@ export function parsePathname(pathname?: string): Segment[] {
         }
       }
 
-      if (part.charAt(0) === '$') {
+      if (part.includes('$')) {
         return {
           type: 'param',
           value: part,
@@ -138,7 +138,8 @@ export function interpolatePath(
       }
 
       if (segment.type === 'param') {
-        return params![segment.value.substring(1)] ?? 'undefined'
+        const [p, v, ...s] = segment.value.split('$')
+        return `${p!}${params![v!] ?? ''}${s.join('$')}`
       }
 
       return segment.value
@@ -242,8 +243,20 @@ export function matchByPath(
           if (baseSegment?.value === '/') {
             return false
           }
-          if (baseSegment.value.charAt(0) !== '$') {
-            params[routeSegment.value.substring(1)] = baseSegment.value
+
+          const [p, v, ...suf] = routeSegment.value.split('$')
+          const s = suf.join('$')
+          const staticMatch = matchLocation.caseSensitive
+            ? baseSegment.value.startsWith(p!) && baseSegment.value.endsWith(s)
+            : baseSegment.value.toLowerCase().startsWith(p!.toLowerCase()) &&
+              baseSegment.value.toLowerCase().endsWith(s.toLowerCase())
+          if (!staticMatch) {
+            return false
+          }
+
+          const paramValue = baseSegment.value.slice(p!.length, -s.length)
+          if (!paramValue.startsWith('$')) {
+            params[v!] = paramValue
           }
         }
       }
diff --git a/packages/react-router/src/utils.ts b/packages/react-router/src/utils.ts
index 9ca840d17f..e98e80d15d 100644
--- a/packages/react-router/src/utils.ts
+++ b/packages/react-router/src/utils.ts
@@ -108,12 +108,17 @@ export type DeepAwaited<T> = T extends Promise<infer A>
   ? { [K in A]: DeepAwaited<B> }
   : T
 
+type PathParamMaskSegment<S extends string> =
+  S extends `${infer P}$${string}$${infer S}`
+    ? `${P}${string}${S}`
+    : S extends `${infer P}$${string}`
+    ? `${P}${string}`
+    : S
+
 export type PathParamMask<TRoutePath extends string> =
-  TRoutePath extends `${infer L}/$${infer C}/${infer R}`
-    ? PathParamMask<`${L}/${string}/${R}`>
-    : TRoutePath extends `${infer L}/$${infer C}`
-    ? PathParamMask<`${L}/${string}`>
-    : TRoutePath
+  TRoutePath extends `${infer T}/${infer U}`
+    ? `${PathParamMaskSegment<T>}/${PathParamMask<U>}`
+    : PathParamMaskSegment<TRoutePath>
 
 export type Timeout = ReturnType<typeof setTimeout>