diff --git a/docs/UserGuide.adoc b/docs/UserGuide.adoc
index e94922d1a9fc..2f3939b16006 100644
--- a/docs/UserGuide.adoc
+++ b/docs/UserGuide.adoc
@@ -152,7 +152,7 @@ Selects the 1st person in the results of the `find` command.
 
 === Listing entered commands : `history`
 
-Lists all the commands that you have entered in chronological order. +
+Lists all the commands that you have entered in reverse chronological order. +
 Format: `history`
 
 === Clearing all entries : `clear`
diff --git a/src/main/java/seedu/address/logic/commands/HistoryCommand.java b/src/main/java/seedu/address/logic/commands/HistoryCommand.java
index cf5f38ffb670..b16218635835 100644
--- a/src/main/java/seedu/address/logic/commands/HistoryCommand.java
+++ b/src/main/java/seedu/address/logic/commands/HistoryCommand.java
@@ -2,6 +2,7 @@
 
 import static java.util.Objects.requireNonNull;
 
+import java.util.Collections;
 import java.util.List;
 
 import seedu.address.logic.CommandHistory;
@@ -13,7 +14,7 @@
 public class HistoryCommand extends Command {
 
     public static final String COMMAND_WORD = "history";
-    public static final String MESSAGE_SUCCESS = "Entered commands (from earliest to most recent):\n%1$s";
+    public static final String MESSAGE_SUCCESS = "Entered commands (from most recent to earliest):\n%1$s";
     public static final String MESSAGE_NO_HISTORY = "You have not yet entered any commands.";
 
     @Override
@@ -24,6 +25,7 @@ public CommandResult execute() {
             return new CommandResult(MESSAGE_NO_HISTORY);
         }
 
+        Collections.reverse(previousCommands);
         return new CommandResult(String.format(MESSAGE_SUCCESS, String.join("\n", previousCommands)));
     }
 
diff --git a/src/test/java/seedu/address/logic/commands/HistoryCommandTest.java b/src/test/java/seedu/address/logic/commands/HistoryCommandTest.java
index 17952be1d061..8bdf3f75ffe2 100644
--- a/src/test/java/seedu/address/logic/commands/HistoryCommandTest.java
+++ b/src/test/java/seedu/address/logic/commands/HistoryCommandTest.java
@@ -35,7 +35,7 @@ public void execute() {
         history.add(command3);
 
         String expectedMessage = String.format(HistoryCommand.MESSAGE_SUCCESS,
-                String.join("\n", command1, command2, command3));
+                String.join("\n", command3, command2, command1));
 
         assertCommandResult(historyCommand, expectedMessage);
     }