diff --git a/modules/openapi-generator/src/main/java/org/openapitools/codegen/languages/PythonLegacyClientCodegen.java b/modules/openapi-generator/src/main/java/org/openapitools/codegen/languages/PythonLegacyClientCodegen.java
index c2955c34e1a..fbefdec4253 100644
--- a/modules/openapi-generator/src/main/java/org/openapitools/codegen/languages/PythonLegacyClientCodegen.java
+++ b/modules/openapi-generator/src/main/java/org/openapitools/codegen/languages/PythonLegacyClientCodegen.java
@@ -797,9 +797,7 @@ public class PythonLegacyClientCodegen extends DefaultCodegen implements Codegen
             if ("Number".equalsIgnoreCase(schema.getFormat())) {return "1";}
             if (StringUtils.isNotBlank(schema.getPattern())) {
                 String pattern = schema.getPattern();
-                while (pattern.startsWith("/")) pattern = pattern.substring(0, pattern.length()-1);
-                while (pattern.endsWith("/")) pattern = pattern.substring(1);
-                RgxGen rgxGen = new RgxGen(pattern);
+                RgxGen rgxGen = new RgxGen(patternCorrection(pattern));
                 // this seed makes it so if we have [a-z] we pick a
                 Random random = new Random(18);
                 String sample = rgxGen.generate(random);
@@ -1052,4 +1050,14 @@ public class PythonLegacyClientCodegen extends DefaultCodegen implements Codegen
             }
         }
     }
+
+    public String patternCorrection(String pattern){
+        // Java does not recognize starting and ending forward slashes and mode modifiers
+        // It considers them as characters with no special meaning and tries to find them in the match string
+        boolean checkEnding = pattern.endsWith("/i") || pattern.endsWith("/g") || pattern.endsWith("/m");
+        if (checkEnding) pattern = pattern.substring(0, pattern.length()-2);
+        if (pattern.endsWith("/")) pattern = pattern.substring(0, pattern.length()-1);
+        if (pattern.startsWith("/")) pattern = pattern.substring(1);
+        return pattern;
+    }
 }
diff --git a/modules/openapi-generator/src/test/java/org/openapitools/codegen/python/PythonLegacyClientCodegenTest.java b/modules/openapi-generator/src/test/java/org/openapitools/codegen/python/PythonLegacyClientCodegenTest.java
index 15bd68e7f74..f7e949e5f27 100644
--- a/modules/openapi-generator/src/test/java/org/openapitools/codegen/python/PythonLegacyClientCodegenTest.java
+++ b/modules/openapi-generator/src/test/java/org/openapitools/codegen/python/PythonLegacyClientCodegenTest.java
@@ -18,17 +18,20 @@
 package org.openapitools.codegen.python;
 
 import com.google.common.collect.Sets;
+import com.sun.org.apache.xpath.internal.operations.Bool;
 import io.swagger.v3.oas.models.OpenAPI;
 import io.swagger.v3.oas.models.Operation;
 import io.swagger.v3.oas.models.media.*;
 import io.swagger.v3.parser.util.SchemaTypeUtil;
 import org.openapitools.codegen.*;
 import org.openapitools.codegen.languages.PythonLegacyClientCodegen;
+import org.openapitools.codegen.utils.ModelUtils;
 import org.testng.Assert;
 import org.testng.annotations.Test;
 
 import java.util.ArrayList;
 import java.util.Arrays;
+import java.util.regex.Pattern;
 
 public class PythonLegacyClientCodegenTest {
 
@@ -93,6 +96,25 @@ public class PythonLegacyClientCodegenTest {
         Assert.assertEquals(op.allParams.get(5).pattern, "/^pattern\\d{3}$/i");
     }
 
+
+
+    @Test(description = "test generated example values for string properties")
+    public void testGeneratedExampleValues() {
+        final OpenAPI openAPI = TestUtils.parseFlattenSpec("src/test/resources/3_0/examples.yaml");
+        final PythonLegacyClientCodegen codegen = new PythonLegacyClientCodegen();
+        codegen.setOpenAPI(openAPI);
+        final Schema dummyUserSchema = openAPI.getComponents().getSchemas().get("DummyUser");
+        final Schema nameSchema = (Schema) dummyUserSchema.getProperties().get("name");
+        final Schema numberSchema = (Schema) dummyUserSchema.getProperties().get("number");
+        final Schema addressSchema = (Schema) dummyUserSchema.getProperties().get("address");
+        final String namePattern = codegen.patternCorrection(nameSchema.getPattern());
+        final String numberPattern = codegen.patternCorrection(numberSchema.getPattern());
+        final String addressPattern = codegen.patternCorrection(addressSchema.getPattern());
+        Assert.assertTrue(codegen.escapeQuotationMark(codegen.toExampleValue(nameSchema)).matches(namePattern));
+        Assert.assertTrue(codegen.escapeQuotationMark(codegen.toExampleValue(numberSchema)).matches(numberPattern));
+        Assert.assertTrue(codegen.escapeQuotationMark(codegen.toExampleValue(addressSchema)).matches(addressPattern));
+    }
+
     @Test(description = "test single quotes escape")
     public void testSingleQuotes() {
         final PythonLegacyClientCodegen codegen = new PythonLegacyClientCodegen();
diff --git a/modules/openapi-generator/src/test/resources/3_0/examples.yaml b/modules/openapi-generator/src/test/resources/3_0/examples.yaml
index dd1b88d52c2..07893343180 100644
--- a/modules/openapi-generator/src/test/resources/3_0/examples.yaml
+++ b/modules/openapi-generator/src/test/resources/3_0/examples.yaml
@@ -118,3 +118,15 @@ components:
           properties:
             city:
               type: string
+    DummyUser:
+      type: object
+      properties:
+        name:
+          type: string
+          pattern: '/^[a-z\s]+$/'
+        number:
+          type: string
+          pattern: '/[0-9]{10}/g'
+        address:
+          type: string
+          pattern: '/^[a-z0-9\s]+$/i'