diff --git a/pkg/sql/logictest/testdata/logic_test/tsvector b/pkg/sql/logictest/testdata/logic_test/tsvector
index 6e4bbff5b1b2..f910ec6bcf33 100644
--- a/pkg/sql/logictest/testdata/logic_test/tsvector
+++ b/pkg/sql/logictest/testdata/logic_test/tsvector
@@ -360,3 +360,78 @@ LIMIT
 	2
 ----
 0
+
+subtest 98804_regression_test
+
+statement ok
+RESET default_text_search_config
+
+statement ok
+CREATE TABLE ab (a TEXT, b TEXT)
+
+statement ok
+INSERT INTO ab VALUES('fat rats', 'fat cats chased fat, out of shape rats');
+
+query B
+SELECT a @@ b FROM ab
+----
+false
+
+query B
+SELECT b @@ a FROM ab
+----
+true
+
+query B
+SELECT 'fat rats' @@ b FROM ab
+----
+false
+
+query B
+SELECT b @@ 'fat rats' FROM ab
+----
+true
+
+query B
+SELECT a @@ 'fat cats ate fat bats' FROM ab
+----
+false
+
+query B
+SELECT 'fat cats ate fat bats' @@ a FROM ab
+----
+false
+
+statement error pgcode 22023 unsupported comparison operator: <string> @@ <tsvector>
+SELECT b @@ a::tsvector FROM ab
+
+statement error pgcode 22023 unsupported comparison operator: <tsvector> @@ <string>
+SELECT a::tsvector @@ b FROM ab
+
+query B
+SELECT 'fat bat cat' @@ 'bats fats'
+----
+true
+
+query B
+SELECT 'bats fats' @@ 'fat bat cat'
+----
+false
+
+query B
+SELECT 'fat' @@ 'fat rats'::tsvector
+----
+true
+
+# TODO(#75101): The error should be "syntax error in TSQuery".
+statement error pgcode 22023 unsupported comparison operator: <string> @@ <tsvector>
+SELECT 'fat cats chased fat, out of shape rats' @@ 'fat rats'::tsvector
+
+query B
+SELECT 'fat rats'::tsvector @@ 'fat'
+----
+true
+
+# TODO(#75101): The error should be "syntax error in TSQuery".
+statement error pgcode 22023 unsupported comparison operator: <tsvector> @@ <string>
+SELECT 'fat rats'::tsvector @@ 'fat cats chased fat, out of shape rats'
diff --git a/pkg/sql/sem/tree/overload.go b/pkg/sql/sem/tree/overload.go
index 8cc2be0648b5..7a0be0d6ead7 100644
--- a/pkg/sql/sem/tree/overload.go
+++ b/pkg/sql/sem/tree/overload.go
@@ -997,7 +997,7 @@ func (s *overloadTypeChecker) typeCheckOverloadedExprs(
 			return err
 		}
 
-		// The fourth heuristic is to prefer candidates that accepts the "best"
+		// The fourth heuristic is to prefer candidates that accept the "best"
 		// mutual type in the resolvable type set of all constants.
 		if bestConstType, ok := commonConstantType(s.exprs, s.constIdxs); ok {
 			// In case all overloads are filtered out at this step,
diff --git a/pkg/sql/sem/tree/type_check.go b/pkg/sql/sem/tree/type_check.go
index fa71894b2fbd..85f4482a8051 100644
--- a/pkg/sql/sem/tree/type_check.go
+++ b/pkg/sql/sem/tree/type_check.go
@@ -2204,6 +2204,38 @@ func typeCheckComparisonOp(
 	_, leftIsTuple := foldedLeft.(*Tuple)
 	_, rightIsTuple := foldedRight.(*Tuple)
 	_, rightIsSubquery := foldedRight.(SubqueryExpr)
+	var tsMatchesWithText bool
+	var typedLeft, typedRight TypedExpr
+	var leftFamily, rightFamily types.Family
+	var err error
+
+	// Do an initial check for TEXT @@ XXX special cases which might need to
+	// inject a to_tsvector or plainto_tsquery function call.
+	if op.Symbol == treecmp.TSMatches {
+		if switched {
+			// The order of operators matters as to which function call to apply.
+			foldedLeft, foldedRight = foldedRight, foldedLeft
+			switched = false
+		}
+		disallowSwitch = true
+		typedLeft, err = foldedLeft.TypeCheck(ctx, semaCtx, types.Any)
+		if err != nil {
+			sigWithErr := fmt.Sprintf(compExprsFmt, left, op, right, err)
+			return nil, nil, nil, false,
+				pgerror.Newf(pgcode.InvalidParameterValue, unsupportedCompErrFmt, sigWithErr)
+		}
+		typedRight, err = foldedRight.TypeCheck(ctx, semaCtx, types.Any)
+		if err != nil {
+			sigWithErr := fmt.Sprintf(compExprsFmt, left, op, right, err)
+			return nil, nil, nil, false,
+				pgerror.Newf(pgcode.InvalidParameterValue, unsupportedCompErrFmt, sigWithErr)
+		}
+		leftFamily = typedLeft.ResolvedType().Family()
+		rightFamily = typedRight.ResolvedType().Family()
+		if leftFamily == types.StringFamily || rightFamily == types.StringFamily {
+			tsMatchesWithText = true
+		}
+	}
 
 	handleTupleTypeMismatch := false
 	switch {
@@ -2227,7 +2259,7 @@ func typeCheckComparisonOp(
 				pgerror.Newf(pgcode.InvalidParameterValue, unsupportedCompErrFmt, sig)
 		}
 
-		typedLeft := typedSubExprs[0]
+		typedLeft = typedSubExprs[0]
 		typedSubExprs = typedSubExprs[1:]
 
 		rightTuple.typ = types.MakeTuple(make([]*types.T, len(typedSubExprs)))
@@ -2241,7 +2273,7 @@ func typeCheckComparisonOp(
 		return typedLeft, rightTuple, fn, false, nil
 
 	case foldedOp.Symbol == treecmp.In && rightIsSubquery:
-		typedLeft, err := foldedLeft.TypeCheck(ctx, semaCtx, types.Any)
+		typedLeft, err = foldedLeft.TypeCheck(ctx, semaCtx, types.Any)
 		if err != nil {
 			sigWithErr := fmt.Sprintf(compExprsFmt, left, op, right, err)
 			return nil, nil, nil, false,
@@ -2257,14 +2289,14 @@ func typeCheckComparisonOp(
 		}
 
 		desired := types.MakeTuple([]*types.T{typ})
-		typedRight, err := foldedRight.TypeCheck(ctx, semaCtx, desired)
+		typedRight, err = foldedRight.TypeCheck(ctx, semaCtx, desired)
 		if err != nil {
 			sigWithErr := fmt.Sprintf(compExprsFmt, left, op, right, err)
 			return nil, nil, nil, false,
 				pgerror.Newf(pgcode.InvalidParameterValue, unsupportedCompErrFmt, sigWithErr)
 		}
 
-		if err := typeCheckSubqueryWithIn(
+		if err = typeCheckSubqueryWithIn(
 			typedLeft.ResolvedType(), typedRight.ResolvedType(),
 		); err != nil {
 			return nil, nil, nil, false, err
@@ -2279,16 +2311,17 @@ func typeCheckComparisonOp(
 				pgerror.Newf(pgcode.InvalidParameterValue, unsupportedCompErrFmt, sig)
 		}
 		// Using non-folded left and right to avoid having to swap later.
-		typedLeft, typedRight, err := typeCheckTupleComparison(ctx, semaCtx, op, left.(*Tuple), right.(*Tuple))
+		typedLeft, typedRight, err = typeCheckTupleComparison(ctx, semaCtx, op, left.(*Tuple), right.(*Tuple))
 		if err != nil {
 			return nil, nil, nil, false, err
 		}
 		return typedLeft, typedRight, fn, false, nil
 
 	case leftIsTuple || rightIsTuple:
+		var errLeft, errRight error
 		// Tuple must compare with a tuple type, as handled above.
-		typedLeft, errLeft := foldedLeft.TypeCheck(ctx, semaCtx, types.Any)
-		typedRight, errRight := foldedRight.TypeCheck(ctx, semaCtx, types.Any)
+		typedLeft, errLeft = foldedLeft.TypeCheck(ctx, semaCtx, types.Any)
+		typedRight, errRight = foldedRight.TypeCheck(ctx, semaCtx, types.Any)
 		if errLeft == nil && errRight == nil &&
 			((typedLeft.ResolvedType().Family() == types.TupleFamily &&
 				typedRight.ResolvedType().Family() != types.TupleFamily) ||
@@ -2296,6 +2329,36 @@ func typeCheckComparisonOp(
 					typedLeft.ResolvedType().Family() != types.TupleFamily)) {
 			handleTupleTypeMismatch = true
 		}
+	case tsMatchesWithText:
+		// Apply rules from:
+		// https://www.postgresql.org/docs/current/textsearch-intro.html#TEXTSEARCH-MATCHING
+		// Perform the following type conversions:
+		//            initial             |              result
+		// -------------------------------------------------------------------------
+		// a::TEXT @@ b::TEXT             |  to_tsvector(a) @@ plainto_tsquery(b)
+		// a::TEXT @@ b::TSQUERY          |  to_tsvector(a) @@ b
+		// a::TSQUERY @@ b::TEXT          |  a @@ to_tsvector(b)
+		// a::TSVECTOR @@ b::TEXT         |  a @@ b::TSQUERY
+		// a::TEXT @@ b::TSVECTOR         |  a::TSQUERY @@ b
+		if leftFamily == types.StringFamily {
+			if rightFamily == types.StringFamily || rightFamily == types.TSQueryFamily {
+				leftExprs := make(Exprs, 1)
+				leftExprs[0] = typedLeft
+				foldedLeft = &FuncExpr{Func: WrapFunction("to_tsvector"), Exprs: leftExprs, AggType: GeneralAgg}
+			}
+		}
+
+		funcName := "plainto_tsquery"
+		if rightFamily == types.StringFamily {
+			if leftFamily == types.StringFamily || leftFamily == types.TSQueryFamily {
+				if leftFamily == types.TSQueryFamily {
+					funcName = "to_tsvector"
+				}
+				rightExprs := make(Exprs, 1)
+				rightExprs[0] = typedRight
+				foldedRight = &FuncExpr{Func: WrapFunction(funcName), Exprs: rightExprs, AggType: GeneralAgg}
+			}
+		}
 	}
 
 	// For comparisons, we do not stimulate the typing of untyped NULL with the
@@ -2356,8 +2419,8 @@ func typeCheckComparisonOp(
 	}
 	leftReturn := leftExpr.ResolvedType()
 	rightReturn := rightExpr.ResolvedType()
-	leftFamily := leftReturn.Family()
-	rightFamily := rightReturn.Family()
+	leftFamily = leftReturn.Family()
+	rightFamily = rightReturn.Family()
 
 	// Return early if at least one overload is possible, NULL is an argument,
 	// and none of the overloads accept NULL.
diff --git a/pkg/sql/sem/tree/type_check_test.go b/pkg/sql/sem/tree/type_check_test.go
index ea9910e1db10..58a71e41ffdb 100644
--- a/pkg/sql/sem/tree/type_check_test.go
+++ b/pkg/sql/sem/tree/type_check_test.go
@@ -213,6 +213,13 @@ func TestTypeCheck(t *testing.T) {
 
 		// String preference.
 		{`st_geomfromgeojson($1)`, `st_geomfromgeojson($1:::STRING):::GEOMETRY`},
+
+		// TSQuery and TSVector
+		{`'a' @@ 'b'`, `to_tsvector('a':::STRING) @@ plainto_tsquery('b':::STRING)`},
+		{`'a' @@ 'b':::TSQUERY`, `to_tsvector('a':::STRING) @@ '''b''':::TSQUERY`},
+		{`'a':::TSQUERY @@ 'b'`, `'''a''':::TSQUERY @@ to_tsvector('b':::STRING)`},
+		{`'a' @@ 'b':::TSVECTOR`, `'''a''':::TSQUERY @@ '''b''':::TSVECTOR`},
+		{`'a':::TSVECTOR @@ 'b'`, `'''a''':::TSVECTOR @@ '''b''':::TSQUERY`},
 	}
 	ctx := context.Background()
 	for _, d := range testData {