diff --git a/x-pack/plugin/esql/src/main/java/org/elasticsearch/xpack/esql/evaluator/predicate/operator/comparison/EsqlBinaryComparison.java b/x-pack/plugin/esql/src/main/java/org/elasticsearch/xpack/esql/evaluator/predicate/operator/comparison/EsqlBinaryComparison.java
index 71c487b567344..1750c4bd8f1e1 100644
--- a/x-pack/plugin/esql/src/main/java/org/elasticsearch/xpack/esql/evaluator/predicate/operator/comparison/EsqlBinaryComparison.java
+++ b/x-pack/plugin/esql/src/main/java/org/elasticsearch/xpack/esql/evaluator/predicate/operator/comparison/EsqlBinaryComparison.java
@@ -123,12 +123,6 @@ protected TypeResolution checkCompatibility() {
             return new TypeResolution(formatIncompatibleTypesMessage());
         }
 
-        // String literals (and only literals) can be cast up to dates
-        if ((DataTypes.isDateTime(leftType) && DataTypes.isString(rightType) && right() instanceof Literal)
-            || (DataTypes.isDateTime(rightType) && DataTypes.isString(leftType) && left() instanceof Literal)) {
-            return TypeResolution.TYPE_RESOLVED;
-        }
-
         if ((leftType.isNumeric() && rightType.isNumeric())
             || (DataTypes.isString(leftType) && DataTypes.isString(rightType))
             || leftType.equals(rightType)
diff --git a/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/function/TestCaseSupplier.java b/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/function/TestCaseSupplier.java
index 554f3622577ca..af84dfc1a08e2 100644
--- a/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/function/TestCaseSupplier.java
+++ b/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/function/TestCaseSupplier.java
@@ -945,21 +945,6 @@ public static List<TypedDataSupplier> dateCases() {
         );
     }
 
-    public static List<TypedDataSupplier> datesAsStringLiteralsCases() {
-        List<TypedDataSupplier> cases = new ArrayList<>();
-        for (TypedDataSupplier dateCase : dateCases()) {
-            cases.add(
-                new TypedDataSupplier(
-                    "<" + dateCase.name + "as string>",
-                    () -> EsqlDataTypeConverter.dateTimeToString((long) dateCase.supplier.get()),
-                    DataTypes.KEYWORD,
-                    true
-                )
-            );
-        }
-        return cases;
-    }
-
     public static List<TypedDataSupplier> datePeriodCases() {
         return List.of(
             new TypedDataSupplier("<zero date period>", () -> Period.ZERO, EsqlDataTypes.DATE_PERIOD),
diff --git a/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/EqualsTests.java b/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/EqualsTests.java
index de53195cc0581..1e011d5c915bb 100644
--- a/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/EqualsTests.java
+++ b/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/EqualsTests.java
@@ -128,19 +128,6 @@ public static Iterable<Object[]> parameters() {
             )
         );
 
-        suppliers.addAll(
-            TestCaseSupplier.forBinaryNotCasting(
-                "EqualsLongsEvaluator",
-                "lhs",
-                "rhs",
-                Object::equals,
-                DataTypes.BOOLEAN,
-                TestCaseSupplier.dateCases(),
-                TestCaseSupplier.datesAsStringLiteralsCases(),
-                List.of()
-            )
-        );
-
         List<TestCaseSupplier.TypedDataSupplier> lhsSuppliers = new ArrayList<>();
         List<TestCaseSupplier.TypedDataSupplier> rhsSuppliers = new ArrayList<>();
         for (DataType type : AbstractConvertFunction.STRING_TYPES) {