diff --git a/vllm/v1/engine/core.py b/vllm/v1/engine/core.py
index 43cb95fb47f95..1ba557977707f 100644
--- a/vllm/v1/engine/core.py
+++ b/vllm/v1/engine/core.py
@@ -137,7 +137,7 @@ class EngineCore:
         req = Request.from_engine_core_request(request)
         if req.use_structured_output:
             # Start grammar compilation asynchronously
-            self.structured_output_manager.populate_cache(req)
+            self.structured_output_manager.grammar_init(req)
 
         self.scheduler.add_request(req)
 
diff --git a/vllm/v1/structured_output/__init__.py b/vllm/v1/structured_output/__init__.py
index 3f828e0854765..fd1e6feed6a0b 100644
--- a/vllm/v1/structured_output/__init__.py
+++ b/vllm/v1/structured_output/__init__.py
@@ -1,18 +1,15 @@
 # SPDX-License-Identifier: Apache-2.0
 from __future__ import annotations
 
-import copy
 import multiprocessing
-from collections import OrderedDict
-from concurrent.futures import ThreadPoolExecutor
+from concurrent.futures import Future, ThreadPoolExecutor
 from typing import TYPE_CHECKING, Optional
 
 from vllm.config import VllmConfig
 from vllm.logger import init_logger
 from vllm.transformers_utils.tokenizer_group import init_tokenizer_from_configs
 from vllm.utils import LazyLoader
-from vllm.v1.structured_output.grammar import (Grammar, StructuredOutputKey,
-                                               StructuredOutputOptions)
+from vllm.v1.structured_output.grammar import Grammar, StructuredOutputOptions
 
 if TYPE_CHECKING:
     import numpy as np
@@ -29,7 +26,7 @@ logger = init_logger(__name__)
 
 class StructuredOutputManager:
 
-    def __init__(self, vllm_config: VllmConfig, max_cache_size: int = 500):
+    def __init__(self, vllm_config: VllmConfig):
         tokenizer_group = init_tokenizer_from_configs(
             model_config=vllm_config.model_config,
             scheduler_config=vllm_config.scheduler_config,
@@ -44,10 +41,6 @@ class StructuredOutputManager:
             tokenizer, vocab_size=self.vocab_size)
         self.compiler = xgr.GrammarCompiler(tokenizer_info, max_threads=8)
 
-        self.max_cache_size = max_cache_size
-        self.request_key_to_grammar: OrderedDict[StructuredOutputKey,
-                                                 Grammar] = OrderedDict()
-
         # The default max_workers if not specified is the number of CPUs * 5,
         # which is way too high since these tasks are CPU-bound, not I/O bound.
         # We also know we would never dominate CPU usage with just grammar
@@ -56,51 +49,22 @@ class StructuredOutputManager:
         self.executor = ThreadPoolExecutor(max_workers=max_workers)
         self._grammar_bitmask: Optional[torch.Tensor] = None
 
-    def __getitem__(self, key: StructuredOutputKey) -> Optional[Grammar]:
-        # We need to pop and re-insert the grammar here for LRU cache
-        # of request_key_to_grammar
-        if key in self.request_key_to_grammar:
-            # Move accessed item to the end (most recently used)
-            value = self.request_key_to_grammar.pop(key)
-            if value is not None:
-                self.request_key_to_grammar[key] = value
-            return value
-        return None
-
-    def populate_cache(self, request: Request) -> None:
+    def grammar_init(self, request: Request) -> None:
         if request.structured_output_request is None:
             return
 
-        grammar = self.request_key_to_grammar.get(
-            request.structured_output_request.structured_output_key)
-        if grammar:
-            request.structured_output_request.grammar = copy.copy(grammar)
-            return
-        request.structured_output_request.grammar = self.cache(request)
+        grammar: Future[Grammar] = self.executor.submit(
+            self._async_create_grammar, request)
+        request.structured_output_request.grammar = grammar  # type: ignore[assignment]
 
-    def cache(self, request: Request):
-        return self.executor.submit(self._executor_loop, request)
-
-    def _executor_loop(self, request: Request) -> Grammar:
-        # NOTE: The structured_output_request should never be
-        # None in this case, but mypy can't infer this
-        # correctly, so we need to ignore the error here.
+    def _async_create_grammar(self, request: Request) -> Grammar:
         key = request.structured_output_request.structured_output_key  # type: ignore[union-attr]
-        grammar = self.request_key_to_grammar.get(key)
-        if grammar is not None:
-            return copy.copy(grammar)
-        grammar = self.initialize_grammar(key)
-        # If cache is full, remove the least recently used item
-        if len(self.request_key_to_grammar) >= self.max_cache_size:
-            self.request_key_to_grammar.popitem(last=False)
-        self.request_key_to_grammar[key] = grammar
-        return copy.copy(grammar)
 
-    def initialize_grammar(self, key: StructuredOutputKey) -> Grammar:
         # Note that the request was validated in the engine core client,
         # so at this point we know it is a supported type of request.
         #
-        # TODO: we still need to handle xgrammar compilation failures
+        # TODO: we still need to handle xgrammar compilation failures,
+        # though it should be unlikely as we test that up front as well.
         request_type, grammar_spec = key
 
         if request_type == StructuredOutputOptions.JSON: