diff --git a/Tests/LibRegex/Regex.cpp b/Tests/LibRegex/Regex.cpp
index daeb623c433..2b4da92c983 100644
--- a/Tests/LibRegex/Regex.cpp
+++ b/Tests/LibRegex/Regex.cpp
@@ -690,7 +690,10 @@ TEST_CASE(ECMA262_match)
         { "a|$"sv, "x"sv, true, (ECMAScriptFlags)regex::AllFlags::Global }, // #11940, Global (not the 'g' flag) regexps should attempt to match the zero-length end of the string too.
         { "foo\nbar"sv, "foo\nbar"sv, true }, // #12126, ECMA262 regexp should match literal newlines without the 's' flag.
         { "foo[^]bar"sv, "foo\nbar"sv, true }, // #12126, ECMA262 regexp should match newline with [^].
-        { "^[_A-Z]+$"sv, "_aA"sv, true, ECMAScriptFlags::Insensitive } // Insensitive lookup table: characters in a range do not necessarily lie in the same range after being converted to lowercase.
+        { "^[_A-Z]+$"sv, "_aA"sv, true, ECMAScriptFlags::Insensitive }, // Insensitive lookup table: characters in a range do not necessarily lie in the same range after being converted to lowercase.
+        { "^[a-sy-z]$"sv, "b"sv, true, ECMAScriptFlags::Insensitive },
+        { "^[a-sy-z]$"sv, "y"sv, true, ECMAScriptFlags::Insensitive },
+        { "^[a-sy-z]$"sv, "u"sv, false, ECMAScriptFlags::Insensitive },
     };
     // clang-format on
 
diff --git a/Userland/Libraries/LibRegex/RegexByteCode.cpp b/Userland/Libraries/LibRegex/RegexByteCode.cpp
index ace32620fc4..e0c0ca4a272 100644
--- a/Userland/Libraries/LibRegex/RegexByteCode.cpp
+++ b/Userland/Libraries/LibRegex/RegexByteCode.cpp
@@ -557,11 +557,14 @@ ALWAYS_INLINE ExecutionResult OpCode_Compare::execute(MatchInput const& input, M
                     upper_case_needle = to_ascii_uppercase(needle);
                     lower_case_needle = to_ascii_lowercase(needle);
                 }
-                if (lower_case_needle > range.to && upper_case_needle > range.to)
+
+                if (lower_case_needle >= range.from && lower_case_needle <= range.to)
+                    return 0;
+                if (upper_case_needle >= range.from && upper_case_needle <= range.to)
+                    return 0;
+                if (lower_case_needle > range.to || upper_case_needle > range.to)
                     return 1;
-                if (lower_case_needle < range.from && upper_case_needle < range.from)
-                    return -1;
-                return 0;
+                return -1;
             });
 
             if (matching_range) {