diff --git a/pandas/core/tools/datetimes.py b/pandas/core/tools/datetimes.py
index e23bf6269893d..d8be68d9ccf62 100644
--- a/pandas/core/tools/datetimes.py
+++ b/pandas/core/tools/datetimes.py
@@ -251,6 +251,8 @@ def _maybe_cache(
 
         unique_dates = unique(arg)
         if len(unique_dates) < len(arg):
+            # GH-55345 checking for parse errors
+            convert_listlike(arg, format)
             cache_dates = convert_listlike(unique_dates, format)
             # GH#45319
             try:
diff --git a/pandas/tests/tools/test_to_datetime.py b/pandas/tests/tools/test_to_datetime.py
index aefaba1aed058..f8ed06026d5e5 100644
--- a/pandas/tests/tools/test_to_datetime.py
+++ b/pandas/tests/tools/test_to_datetime.py
@@ -3686,3 +3686,11 @@ def test_to_datetime_with_empty_str_utc_false_offsets_and_format_mixed():
         to_datetime(
             ["2020-01-01 00:00+00:00", "2020-01-01 00:00+02:00", ""], format="mixed"
         )
+
+
+def test_to_datetime_parse_error_for_more_than_50rows():
+    # GH-55345
+    msg = 'when parsing with format "%Y-%m-%d": " 09", at position 50.'
+
+    with pytest.raises(ValueError, match=msg):
+        to_datetime(["2012-01-01"] * 50 + ["2012-01-02 09"])