diff --git a/src/main/java/com/artillexstudios/axtrade/commands/Commands.java b/src/main/java/com/artillexstudios/axtrade/commands/Commands.java
index 0f2de40..8840efe 100644
--- a/src/main/java/com/artillexstudios/axtrade/commands/Commands.java
+++ b/src/main/java/com/artillexstudios/axtrade/commands/Commands.java
@@ -75,11 +75,12 @@ public class Commands implements OrphanCommand {
     @Subcommand("deny")
     public void deny(@NotNull Player sender, @NotNull Player other) {
         var request = Requests.getRequest(sender, other);
-        if (request == null || request.getSender().equals(sender)) {
+        if (request == null || request.getSender().equals(sender) || request.isDeclined()) {
             MESSAGEUTILS.sendLang(sender, "request.no-request", Map.of("%player%", other.getName()));
             return;
         }
 
+        request.decline();
         MESSAGEUTILS.sendLang(request.getSender(), "request.deny-sender", Map.of("%player%", request.getReceiver().getName()));
         MESSAGEUTILS.sendLang(request.getReceiver(), "request.deny-receiver", Map.of("%player%", request.getSender().getName()));
         SoundUtils.playSound(request.getSender(), "deny");
diff --git a/src/main/java/com/artillexstudios/axtrade/request/Request.java b/src/main/java/com/artillexstudios/axtrade/request/Request.java
index b243aa4..c9edde4 100644
--- a/src/main/java/com/artillexstudios/axtrade/request/Request.java
+++ b/src/main/java/com/artillexstudios/axtrade/request/Request.java
@@ -6,6 +6,7 @@ public class Request {
     private final long time;
     private final Player sender;
     private final Player receiver;
+    private boolean declined = false;
 
     public Request(Player sender, Player receiver) {
         this.time = System.currentTimeMillis();
@@ -24,4 +25,12 @@ public class Request {
     public Player getSender() {
         return sender;
     }
+
+    public boolean isDeclined() {
+        return declined;
+    }
+
+    public void decline() {
+        declined = true;
+    }
 }
diff --git a/src/main/java/com/artillexstudios/axtrade/request/Requests.java b/src/main/java/com/artillexstudios/axtrade/request/Requests.java
index 2d8584d..b1f734b 100644
--- a/src/main/java/com/artillexstudios/axtrade/request/Requests.java
+++ b/src/main/java/com/artillexstudios/axtrade/request/Requests.java
@@ -58,16 +58,17 @@ public class Requests {
             return;
         }
 
-        var request = Requests.getRequest(sender, receiver);
-        if (request != null && !request.getSender().equals(sender)) {
-            Trades.addTrade(sender, receiver);
-            requests.remove(request);
-            return;
-        }
-
-        if (request != null && System.currentTimeMillis() - request.getTime() < CONFIG.getInt("trade-request-expire-seconds", 60) * 1_000L) {
-            MESSAGEUTILS.sendLang(sender, "request.already-sent", replacements);
-            return;
+        final Request request = Requests.getRequest(sender, receiver);
+        if (request != null) {
+            if (!request.getSender().equals(sender)) {
+                Trades.addTrade(sender, receiver);
+                requests.remove(request);
+                return;
+            }
+            if (request.isDeclined() || System.currentTimeMillis() - request.getTime() < CONFIG.getInt("trade-request-expire-seconds", 60) * 1_000L) {
+                MESSAGEUTILS.sendLang(sender, "request.already-sent", replacements);
+                return;
+            }
         }
 
         final AxTradeRequestEvent apiEvent = new AxTradeRequestEvent(sender, receiver);