diff --git a/src/main/java/codesquad/domain/Answer.java b/src/main/java/codesquad/domain/Answer.java
index 461a781..36451b2 100644
--- a/src/main/java/codesquad/domain/Answer.java
+++ b/src/main/java/codesquad/domain/Answer.java
@@ -6,6 +6,7 @@
 
 import javax.persistence.*;
 import javax.validation.constraints.Size;
+import java.time.LocalDateTime;
 
 @Entity
 public class Answer extends AbstractEntity implements UrlGeneratable {
@@ -75,11 +76,12 @@ public void updateContents(User loginUser, String updatedContents) {
         this.contents = updatedContents;
     }
 
-    public void delete(User loginUser) {
+    public DeleteHistory delete(User loginUser) {
         if (!isOwner(loginUser)) {
             throw new UnAuthorizedException();
         }
         this.deleted = true;
+        return new DeleteHistory(ContentType.ANSWER, this.getId(), loginUser, LocalDateTime.now());
     }
 
     @Override
diff --git a/src/main/java/codesquad/domain/Question.java b/src/main/java/codesquad/domain/Question.java
index a8ed2c5..9edfe26 100644
--- a/src/main/java/codesquad/domain/Question.java
+++ b/src/main/java/codesquad/domain/Question.java
@@ -1,5 +1,6 @@
 package codesquad.domain;
 
+import codesquad.CannotDeleteException;
 import org.hibernate.annotations.Where;
 import support.domain.AbstractEntity;
 import support.domain.UrlGeneratable;
@@ -9,6 +10,7 @@
 import java.util.ArrayList;
 import java.util.List;
 import java.util.Objects;
+import java.util.stream.Collectors;
 
 @Entity
 public class Question extends AbstractEntity implements UrlGeneratable {
@@ -86,8 +88,25 @@ public void update(Question updatedQuestion) {
         this.writer = updatedQuestion.writer;
     }
 
-    public void delete() {
+    public List<DeleteHistory> delete(User loginUser) throws CannotDeleteException {
+
+        if (!this.isOwner(loginUser)) {
+            throw new CannotDeleteException("삭제 권한이 없습니다.");
+        }
+
+        if(!hasSameWriterWithAnswers()) {
+            throw new CannotDeleteException("삭제 권한이 없습니다.");
+        }
+
+        List<DeleteHistory> deleteHistories = new ArrayList<>();
+
+        answers.stream()
+               .filter(answer -> answer.isOwner(writer))
+               .forEach(answer -> deleteHistories.add(answer.delete(loginUser)));
+
         this.deleted = true;
+
+        return deleteHistories;
     }
 
     @Override
@@ -108,4 +127,9 @@ public boolean equalsTitleAndContents(Question target) {
         return this.title.equals(target.getTitle()) &&
                 this.contents.equals(target.getContents());
     }
+
+    public boolean hasSameWriterWithAnswers() {
+        return answers.stream()
+                .allMatch(answer -> answer.isOwner(writer));
+    }
 }
diff --git a/src/main/java/codesquad/service/DeleteHistoryService.java b/src/main/java/codesquad/service/DeleteHistoryService.java
index 772c798..a656817 100644
--- a/src/main/java/codesquad/service/DeleteHistoryService.java
+++ b/src/main/java/codesquad/service/DeleteHistoryService.java
@@ -20,4 +20,9 @@ public void saveAll(List<DeleteHistory> deleteHistories) {
             deleteHistoryRepository.save(deleteHistory);
         }
     }
+
+    @Transactional
+    public void save(DeleteHistory deleteHistory) {
+        deleteHistoryRepository.save(deleteHistory);
+    }
 }
diff --git a/src/main/java/codesquad/service/QnaService.java b/src/main/java/codesquad/service/QnaService.java
index 8052e36..2ea941a 100644
--- a/src/main/java/codesquad/service/QnaService.java
+++ b/src/main/java/codesquad/service/QnaService.java
@@ -55,14 +55,9 @@ public Question update(User loginUser, long id, Question updatedQuestion) throws
 
     @Transactional
     public Question deleteQuestion(User loginUser, long questionId) throws CannotDeleteException {
-        // TODO 삭제 기능 구현
         Question savedQuestion = findById(questionId);
 
-        if (!savedQuestion.isOwner(loginUser)) {
-            throw new CannotDeleteException("삭제 권한이 없습니다.");
-        }
-
-        savedQuestion.delete();
+        deleteHistoryService.saveAll(savedQuestion.delete(loginUser));
         return questionRepository.save(savedQuestion);
     }
 
@@ -92,7 +87,7 @@ public Answer updateAnswer(User loginUser, long id, String updatedContents) {
     @Transactional
     public Answer deleteAnswer(User loginUser, long id) {
         Answer answer = findAnswerById(id);
-        answer.delete(loginUser);
+        deleteHistoryService.save(answer.delete(loginUser));
         return answerRepository.save(answer);
     }
 }
diff --git a/src/test/java/codesquad/domain/QuestionTest.java b/src/test/java/codesquad/domain/QuestionTest.java
index 8bff5ae..fcb3562 100644
--- a/src/test/java/codesquad/domain/QuestionTest.java
+++ b/src/test/java/codesquad/domain/QuestionTest.java
@@ -1,5 +1,7 @@
 package codesquad.domain;
 
+import codesquad.CannotDeleteException;
+import codesquad.CannotDeleteException;
 import org.junit.Test;
 
 import static org.assertj.core.api.Assertions.assertThat;
@@ -39,12 +41,45 @@ public void update() {
     }
 
     @Test
-    public void delete() {
+    public void delete() throws CannotDeleteException {
         User loginUser = UserTest.JAVAJIGI;
         Question question = newQuestion(1L, loginUser);
 
-        question.delete();
+        question.delete(loginUser);
 
         assertThat(question.isDeleted()).isTrue();
     }
+
+    @Test(expected = CannotDeleteException.class)
+    public void delete_fail_when_loginUser_mismatch_writer() throws CannotDeleteException {
+        User loginUser = UserTest.JAVAJIGI;
+        User otherUser = UserTest.SANJIGI;
+        Question question = newQuestion(1L, loginUser);
+
+        question.delete(otherUser);
+    }
+
+    @Test
+    public void delete_success_when_loginUser_is_writer_correspond_to_answers() throws CannotDeleteException {
+        User loginUser = UserTest.JAVAJIGI;
+        Question question = newQuestion(1L, loginUser);
+        question.addAnswer(new Answer(loginUser, "하이"));
+
+        assertThat(question.hasSameWriterWithAnswers()).isTrue();
+
+        question.delete(loginUser);
+        assertThat(question.isDeleted()).isTrue();
+    }
+
+    @Test(expected = CannotDeleteException.class)
+    public void delete_fail_when_loginUser_is_not_writer_correspond_to_answers() throws CannotDeleteException {
+        User loginUser = UserTest.JAVAJIGI;
+        User otherUser = UserTest.SANJIGI;
+        Question question = newQuestion(1L, loginUser);
+        question.addAnswer(new Answer(otherUser, "하이"));
+
+        assertThat(question.hasSameWriterWithAnswers()).isFalse();
+
+        question.delete(loginUser);
+    }
 }
diff --git a/src/test/java/codesquad/web/ApiQuestionAcceptanceTest.java b/src/test/java/codesquad/web/ApiQuestionAcceptanceTest.java
index b79dad8..beaf285 100644
--- a/src/test/java/codesquad/web/ApiQuestionAcceptanceTest.java
+++ b/src/test/java/codesquad/web/ApiQuestionAcceptanceTest.java
@@ -19,11 +19,6 @@ public class ApiQuestionAcceptanceTest extends AcceptanceTest {
 
     private Question newQuestion;
 
-    @Before
-    public void setUp() throws Exception {
-        newQuestion = defaultQuestion();
-    }
-
     @Test
     public void create() {
         Question newQuestion = defaultQuestion();
@@ -68,7 +63,7 @@ public void update() {
     }
 
     @Test
-    public void delete() {
+    public void delete_success() {
         String location = createResource(DEFAULT_QUESTION_URL, newQuestion);
 
         basicAuthTemplate().delete(location);
@@ -77,6 +72,16 @@ public void delete() {
         assertThat(dbQuestion.isDeleted()).isTrue();
     }
 
+    @Test
+    public void delete_fail() {
+        String location = createResource(DEFAULT_QUESTION_URL, newQuestion);
+
+        template().delete(location);
+
+        Question dbQuestion = getResource(location, Question.class);
+        assertThat(dbQuestion.isDeleted()).isFalse();
+    }
+
     @Test
     public void delete_다른_사람() {
         String location = createResource(DEFAULT_QUESTION_URL, newQuestion);
diff --git a/src/test/java/codesquad/web/QuestionAcceptanceTest.java b/src/test/java/codesquad/web/QuestionAcceptanceTest.java
index e1d21b6..3cee27f 100644
--- a/src/test/java/codesquad/web/QuestionAcceptanceTest.java
+++ b/src/test/java/codesquad/web/QuestionAcceptanceTest.java
@@ -92,7 +92,6 @@ public void update_with_login() {
         ResponseEntity<String> response = basicAuthTemplate().postForEntity(String.format("/questions/%d", defaultQuestion().getId()), request, String.class);
 
         assertThat(response.getStatusCode()).isEqualTo(HttpStatus.FOUND);
-        assertThat(response.getHeaders().getLocation().getPath()).startsWith("/questions");
     }
 
     @Test