diff --git a/pkg/sqlite/filter.go b/pkg/sqlite/filter.go
index 40b19fbde..8b29c9a2f 100644
--- a/pkg/sqlite/filter.go
+++ b/pkg/sqlite/filter.go
@@ -311,13 +311,13 @@ func stringCriterionHandler(c *models.StringCriterionInput, column string) crite
 						f.setError(err)
 						return
 					}
-					f.addWhere(column+" regexp ?", c.Value)
+					f.addWhere(fmt.Sprintf("(%s IS NOT NULL AND %[1]s regexp ?)", column), c.Value)
 				case models.CriterionModifierNotMatchesRegex:
 					if _, err := regexp.Compile(c.Value); err != nil {
 						f.setError(err)
 						return
 					}
-					f.addWhere(column+" NOT regexp ?", c.Value)
+					f.addWhere(fmt.Sprintf("(%s IS NULL OR %[1]s NOT regexp ?)", column), c.Value)
 				default:
 					clause, count := getSimpleCriterionClause(modifier, "?")
 
diff --git a/pkg/sqlite/filter_internal_test.go b/pkg/sqlite/filter_internal_test.go
index 957166eba..5677074d7 100644
--- a/pkg/sqlite/filter_internal_test.go
+++ b/pkg/sqlite/filter_internal_test.go
@@ -530,7 +530,7 @@ func TestStringCriterionHandlerMatchesRegex(t *testing.T) {
 	}, column))
 
 	assert.Len(f.whereClauses, 1)
-	assert.Equal(fmt.Sprintf("%[1]s regexp ?", column), f.whereClauses[0].sql)
+	assert.Equal(fmt.Sprintf("(%s IS NOT NULL AND %[1]s regexp ?)", column), f.whereClauses[0].sql)
 	assert.Len(f.whereClauses[0].args, 1)
 	assert.Equal(validValue, f.whereClauses[0].args[0])
 
@@ -558,7 +558,7 @@ func TestStringCriterionHandlerNotMatchesRegex(t *testing.T) {
 	}, column))
 
 	assert.Len(f.whereClauses, 1)
-	assert.Equal(fmt.Sprintf("%[1]s NOT regexp ?", column), f.whereClauses[0].sql)
+	assert.Equal(fmt.Sprintf("(%s IS NULL OR %[1]s NOT regexp ?)", column), f.whereClauses[0].sql)
 	assert.Len(f.whereClauses[0].args, 1)
 	assert.Equal(validValue, f.whereClauses[0].args[0])
 
diff --git a/pkg/sqlite/performer_test.go b/pkg/sqlite/performer_test.go
index 283303be1..c5c7dc6cd 100644
--- a/pkg/sqlite/performer_test.go
+++ b/pkg/sqlite/performer_test.go
@@ -228,6 +228,46 @@ func verifyPerformerAge(t *testing.T, ageCriterion models.IntCriterionInput) {
 	})
 }
 
+func TestPerformerQueryCareerLength(t *testing.T) {
+	const value = "2005"
+	careerLengthCriterion := models.StringCriterionInput{
+		Value:    value,
+		Modifier: models.CriterionModifierEquals,
+	}
+
+	verifyPerformerCareerLength(t, careerLengthCriterion)
+
+	careerLengthCriterion.Modifier = models.CriterionModifierNotEquals
+	verifyPerformerCareerLength(t, careerLengthCriterion)
+
+	careerLengthCriterion.Modifier = models.CriterionModifierMatchesRegex
+	verifyPerformerCareerLength(t, careerLengthCriterion)
+
+	careerLengthCriterion.Modifier = models.CriterionModifierNotMatchesRegex
+	verifyPerformerCareerLength(t, careerLengthCriterion)
+}
+
+func verifyPerformerCareerLength(t *testing.T, criterion models.StringCriterionInput) {
+	withTxn(func(r models.Repository) error {
+		qb := r.Performer()
+		performerFilter := models.PerformerFilterType{
+			CareerLength: &criterion,
+		}
+
+		performers, _, err := qb.Query(&performerFilter, nil)
+		if err != nil {
+			t.Errorf("Error querying performer: %s", err.Error())
+		}
+
+		for _, performer := range performers {
+			cl := performer.CareerLength
+			verifyNullString(t, cl, criterion)
+		}
+
+		return nil
+	})
+}
+
 func queryPerformers(t *testing.T, qb models.PerformerReader, performerFilter *models.PerformerFilterType, findFilter *models.FindFilterType) []*models.Performer {
 	performers, _, err := qb.Query(performerFilter, findFilter)
 	if err != nil {
diff --git a/pkg/sqlite/query.go b/pkg/sqlite/query.go
index d0d764337..82a17cf4f 100644
--- a/pkg/sqlite/query.go
+++ b/pkg/sqlite/query.go
@@ -1,6 +1,7 @@
 package sqlite
 
 import (
+	"fmt"
 	"regexp"
 
 	"github.com/stashapp/stash/pkg/models"
@@ -127,14 +128,14 @@ func (qb *queryBuilder) handleStringCriterionInput(c *models.StringCriterionInpu
 					qb.err = err
 					return
 				}
-				qb.addWhere(column + " regexp ?")
+				qb.addWhere(fmt.Sprintf("(%s IS NOT NULL AND %[1]s regexp ?)", column))
 				qb.addArg(c.Value)
 			case models.CriterionModifierNotMatchesRegex:
 				if _, err := regexp.Compile(c.Value); err != nil {
 					qb.err = err
 					return
 				}
-				qb.addWhere(column + " NOT regexp ?")
+				qb.addWhere(fmt.Sprintf("(%s IS NULL OR %[1]s NOT regexp ?)", column))
 				qb.addArg(c.Value)
 			case models.CriterionModifierIsNull:
 				qb.addWhere("(" + column + " IS NULL OR TRIM(" + column + ") = '')")
diff --git a/pkg/sqlite/scene_test.go b/pkg/sqlite/scene_test.go
index 153967d1a..ac34403fb 100644
--- a/pkg/sqlite/scene_test.go
+++ b/pkg/sqlite/scene_test.go
@@ -356,6 +356,17 @@ func verifyNullString(t *testing.T, value sql.NullString, criterion models.Strin
 	if criterion.Modifier == models.CriterionModifierNotEquals {
 		assert.NotEqual(criterion.Value, value.String)
 	}
+	if criterion.Modifier == models.CriterionModifierMatchesRegex {
+		assert.True(value.Valid)
+		assert.Regexp(regexp.MustCompile(criterion.Value), value)
+	}
+	if criterion.Modifier == models.CriterionModifierNotMatchesRegex {
+		if !value.Valid {
+			// correct
+			return
+		}
+		assert.NotRegexp(regexp.MustCompile(criterion.Value), value)
+	}
 }
 
 func verifyString(t *testing.T, value string, criterion models.StringCriterionInput) {
diff --git a/pkg/sqlite/setup_test.go b/pkg/sqlite/setup_test.go
index 910ba6413..323bb113c 100644
--- a/pkg/sqlite/setup_test.go
+++ b/pkg/sqlite/setup_test.go
@@ -587,6 +587,15 @@ func getPerformerBirthdate(index int) string {
 	return birthdate.Format("2006-01-02")
 }
 
+func getPerformerCareerLength(index int) *string {
+	if index%5 == 0 {
+		return nil
+	}
+
+	ret := fmt.Sprintf("20%2d", index)
+	return &ret
+}
+
 //createPerformers creates n performers with plain Name and o performers with camel cased NaMe included
 func createPerformers(pqb models.PerformerReaderWriter, n int, o int) error {
 	const namePlain = "Name"
@@ -613,6 +622,11 @@ func createPerformers(pqb models.PerformerReaderWriter, n int, o int) error {
 			},
 		}
 
+		careerLength := getPerformerCareerLength(i)
+		if careerLength != nil {
+			performer.CareerLength = models.NullString(*careerLength)
+		}
+
 		created, err := pqb.Create(performer)
 
 		if err != nil {
diff --git a/ui/v2.5/src/components/Changelog/versions/v060.md b/ui/v2.5/src/components/Changelog/versions/v060.md
index 539043e72..d7f4278d6 100644
--- a/ui/v2.5/src/components/Changelog/versions/v060.md
+++ b/ui/v2.5/src/components/Changelog/versions/v060.md
@@ -20,6 +20,7 @@
 * Added Rescan button to scene, image, gallery details overflow button.
 
 ### 🐛 Bug fixes
+* Fix SQL error when filtering nullable string fields with regex.
 * Fix incorrect folders being excluded during scanning.
 * Filter out streaming resolution options that are over the maximum streaming resolution.
 * Fix `cover.jpg` not being detected as cover image when in sub-directory.