diff --git a/sql/collations.go b/sql/collations.go
index 5febdb8836..6cba60df71 100644
--- a/sql/collations.go
+++ b/sql/collations.go
@@ -16,6 +16,7 @@ package sql
 
 import (
 	"fmt"
+	"io"
 	"unicode/utf8"
 
 	"github.com/cespare/xxhash"
@@ -813,16 +814,15 @@ func (c CollationID) Collation() Collation {
 	return collationArray[c]
 }
 
-// HashToUint returns a hash of the given decoded string based on the collation. Collations take each rune's weight into
-// account, therefore two strings with technically different contents may hash to the same value, as the collation
+// WriteWeightString writes the weights of each codepoint in the string into the given io.Writer.
+// Two strings with technically different contents may generate the same WeightString to the same value, as the collation
 // considers them the same string.
-func (c CollationID) HashToUint(str string) (uint64, error) {
-	hash := xxhash.New()
+func (c CollationID) WriteWeightString(hash io.Writer, str string) error {
 	if c == Collation_binary {
 		// Binary strings are almost always malformed due to their usage, therefore we treat them differently
 		_, err := hash.Write(encodings.StringToBytes(str))
 		if err != nil {
-			return 0, err
+			return err
 		}
 	} else {
 		getRuneWeight := collationArray[c].Sorter
@@ -830,7 +830,7 @@ func (c CollationID) HashToUint(str string) (uint64, error) {
 			// All strings (should) have been decoded at this point, so we can rely on Go's internal string encoding
 			runeFromString, strRead := utf8.DecodeRuneInString(str)
 			if strRead == 0 || strRead == utf8.RuneError {
-				return 0, ErrCollationMalformedString.New("hashing")
+				return ErrCollationMalformedString.New("hashing")
 			}
 			runeWeight := getRuneWeight(runeFromString)
 			_, err := hash.Write([]byte{
@@ -840,11 +840,23 @@ func (c CollationID) HashToUint(str string) (uint64, error) {
 				byte(runeWeight >> 24),
 			})
 			if err != nil {
-				return 0, err
+				return err
 			}
 			str = str[strRead:]
 		}
 	}
+	return nil
+}
+
+// HashToUint returns a hash of the given decoded string based on the collation. Collations take each rune's weight into
+// account, therefore two strings with technically different contents may hash to the same value, as the collation
+// considers them the same string.
+func (c CollationID) HashToUint(str string) (uint64, error) {
+	hash := xxhash.New()
+	err := c.WriteWeightString(hash, str)
+	if err != nil {
+		return 0, err
+	}
 	return hash.Sum64(), nil
 }
 
diff --git a/sql/plan/group_by.go b/sql/plan/group_by.go
index 91d0ee20b0..7e33130f54 100644
--- a/sql/plan/group_by.go
+++ b/sql/plan/group_by.go
@@ -420,12 +420,25 @@ func groupingKey(
 	row sql.Row,
 ) (uint64, error) {
 	hash := xxhash.New()
-	for _, expr := range exprs {
+	for i, expr := range exprs {
 		v, err := expr.Eval(ctx, row)
 		if err != nil {
 			return 0, err
 		}
-		_, err = hash.Write(([]byte)(fmt.Sprintf("%v,", v)))
+
+		if i > 0 {
+			// separate each expression in the grouping key with a nil byte
+			if _, err = hash.Write([]byte{0}); err != nil {
+				return 0, err
+			}
+		}
+
+		switch t := expr.Type().(type) {
+		case sql.StringType:
+			err = t.Collation().WriteWeightString(hash, v.(string))
+		default:
+			_, err = fmt.Fprintf(hash, "%v", v)
+		}
 		if err != nil {
 			return 0, err
 		}
diff --git a/sql/plan/group_by_test.go b/sql/plan/group_by_test.go
index f9b996e39d..b68aee737d 100644
--- a/sql/plan/group_by_test.go
+++ b/sql/plan/group_by_test.go
@@ -17,6 +17,7 @@ package plan
 import (
 	"testing"
 
+	"github.com/dolthub/vitess/go/vt/proto/query"
 	"github.com/stretchr/testify/require"
 
 	"github.com/dolthub/go-mysql-server/memory"
@@ -157,6 +158,86 @@ func TestGroupByAggregationGrouping(t *testing.T) {
 	require.Equal(expected, rows)
 }
 
+func TestGroupByCollations(t *testing.T) {
+	tString := sql.MustCreateString(query.Type_VARCHAR, 255, sql.Collation_utf8mb4_0900_ai_ci)
+	tEnum := sql.MustCreateEnumType([]string{"col1_1", "col1_2"}, sql.Collation_utf8mb4_0900_ai_ci)
+	tSet := sql.MustCreateSetType([]string{"col1_1", "col1_2"}, sql.Collation_utf8mb4_0900_ai_ci)
+
+	var testCases = []struct {
+		Type  sql.Type
+		Value func(t *testing.T, v string) any
+	}{
+		{
+			Type:  tString,
+			Value: func(t *testing.T, v string) any { return v },
+		},
+		{
+			Type: tEnum,
+			Value: func(t *testing.T, v string) any {
+				conv, err := tEnum.Convert(v)
+				require.NoError(t, err)
+				return conv
+			},
+		},
+		{
+			Type: tSet,
+			Value: func(t *testing.T, v string) any {
+				conv, err := tSet.Convert(v)
+				require.NoError(t, err)
+				return conv
+			},
+		},
+	}
+
+	for _, tc := range testCases {
+		t.Run(tc.Type.String(), func(t *testing.T) {
+			require := require.New(t)
+			ctx := sql.NewEmptyContext()
+
+			childSchema := sql.Schema{
+				{Name: "col1", Type: tc.Type},
+				{Name: "col2", Type: sql.Int64},
+			}
+
+			child := memory.NewTable("test", sql.NewPrimaryKeySchema(childSchema), nil)
+
+			rows := []sql.Row{
+				sql.NewRow(tc.Value(t, "col1_1"), int64(1111)),
+				sql.NewRow(tc.Value(t, "Col1_1"), int64(1111)),
+				sql.NewRow(tc.Value(t, "col1_2"), int64(4444)),
+				sql.NewRow(tc.Value(t, "col1_1"), int64(1111)),
+				sql.NewRow(tc.Value(t, "Col1_2"), int64(4444)),
+			}
+
+			for _, r := range rows {
+				require.NoError(child.Insert(sql.NewEmptyContext(), r))
+			}
+
+			p := NewGroupBy(
+				[]sql.Expression{
+					aggregation.NewSum(
+						expression.NewGetFieldWithTable(1, sql.Int64, "test", "col2", false),
+					),
+				},
+				[]sql.Expression{
+					expression.NewGetFieldWithTable(0, tc.Type, "test", "col1", false),
+				},
+				NewResolvedTable(child, nil, nil),
+			)
+
+			rows, err := sql.NodeToRows(ctx, p)
+			require.NoError(err)
+
+			expected := []sql.Row{
+				{float64(3333)},
+				{float64(8888)},
+			}
+
+			require.Equal(expected, rows)
+		})
+	}
+}
+
 func BenchmarkGroupBy(b *testing.B) {
 	table := benchmarkTable(b)