diff --git a/CHANGELOG.md b/CHANGELOG.md
index 96087fad69840..19111ecb3d29a 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -184,6 +184,9 @@ The format is based on [Keep a Changelog](http://keepachangelog.com/en/1.0.0/).
 - Changed `DeviceStatsMonitor` to group metrics based on the logger's `group_separator` ([#11254](https://github.com/PyTorchLightning/pytorch-lightning/pull/11254))
 
 
+- Raised `UserWarning` if evaluation is triggered with `best` ckpt and trainer is configured with multiple checkpoint callbacks ([#11274](https://github.com/PyTorchLightning/pytorch-lightning/pull/11274))
+
+
 - `Trainer.logged_metrics` now always contains scalar tensors, even when a Python scalar was logged ([#11270](https://github.com/PyTorchLightning/pytorch-lightning/pull/11270))
 
 
diff --git a/pytorch_lightning/trainer/trainer.py b/pytorch_lightning/trainer/trainer.py
index 5a6f67c9ea0d3..d89ad75411c8c 100644
--- a/pytorch_lightning/trainer/trainer.py
+++ b/pytorch_lightning/trainer/trainer.py
@@ -1381,16 +1381,22 @@ def __set_ckpt_path(self, ckpt_path: Optional[str], model_provided: bool, model_
             ckpt_path = "best"
 
         if ckpt_path == "best":
-            # if user requests the best checkpoint but we don't have it, error
+            if len(self.checkpoint_callbacks) > 1:
+                rank_zero_warn(
+                    f'`.{fn}(ckpt_path="best")` is called with Trainer configured with multiple `ModelCheckpoint`'
+                    " callbacks. It will use the best checkpoint path from first checkpoint callback."
+                )
+
             if not self.checkpoint_callback:
                 raise MisconfigurationException(
                     f'`.{fn}(ckpt_path="best")` is set but `ModelCheckpoint` is not configured.'
                 )
+
             if not self.checkpoint_callback.best_model_path:
                 if self.fast_dev_run:
                     raise MisconfigurationException(
-                        f"You cannot execute `.{fn}()` with `fast_dev_run=True` unless you do"
-                        f" `.{fn}(ckpt_path=PATH)` as no checkpoint path was generated during fitting."
+                        f'You cannot execute `.{fn}(ckpt_path="best")` with `fast_dev_run=True`.'
+                        f" Please pass an exact checkpoint path to `.{fn}(ckpt_path=...)`"
                     )
                 raise MisconfigurationException(
                     f'`.{fn}(ckpt_path="best")` is set but `ModelCheckpoint` is not configured to save the best model.'
diff --git a/tests/trainer/test_trainer.py b/tests/trainer/test_trainer.py
index 52bd2305d74ca..281afae7c30f7 100644
--- a/tests/trainer/test_trainer.py
+++ b/tests/trainer/test_trainer.py
@@ -774,6 +774,21 @@ def predict_step(self, batch, *_):
             trainer_fn(model, ckpt_path="best")
 
 
+def test_best_ckpt_evaluate_raises_warning_with_multiple_ckpt_callbacks():
+    """Test that a warning is raised if best ckpt callback is used for evaluation configured with multiple
+    checkpoints."""
+
+    ckpt_callback1 = ModelCheckpoint()
+    ckpt_callback1.best_model_path = "foo_best_model.ckpt"
+    ckpt_callback2 = ModelCheckpoint()
+    ckpt_callback2.best_model_path = "bar_best_model.ckpt"
+    trainer = Trainer(callbacks=[ckpt_callback1, ckpt_callback2])
+    trainer.state.fn = TrainerFn.TESTING
+
+    with pytest.warns(UserWarning, match="best checkpoint path from first checkpoint callback"):
+        trainer._Trainer__set_ckpt_path(ckpt_path="best", model_provided=False, model_connected=True)
+
+
 def test_disabled_training(tmpdir):
     """Verify that `limit_train_batches=0` disables the training loop unless `fast_dev_run=True`."""
 
@@ -1799,15 +1814,11 @@ def on_fit_start(self, trainer, pl_module: LightningModule) -> None:
     trainer.fit(model, datamodule=dm)
 
 
-def test_exception_when_testing_or_validating_with_fast_dev_run(tmpdir):
-    trainer = Trainer(default_root_dir=tmpdir, fast_dev_run=True)
-    model = BoringModel()
-    trainer.fit(model)
-
-    with pytest.raises(MisconfigurationException, match=r"\.validate\(\)` with `fast_dev_run=True"):
-        trainer.validate()
-    with pytest.raises(MisconfigurationException, match=r"\.test\(\)` with `fast_dev_run=True"):
-        trainer.test()
+def test_exception_when_testing_or_validating_with_fast_dev_run():
+    trainer = Trainer(fast_dev_run=True)
+    trainer.state.fn = TrainerFn.TESTING
+    with pytest.raises(MisconfigurationException, match=r"with `fast_dev_run=True`. .* pass an exact checkpoint path"):
+        trainer._Trainer__set_ckpt_path(ckpt_path="best", model_provided=False, model_connected=True)
 
 
 class TrainerStagesModel(BoringModel):