diff --git a/apps/web/components/booking/bookingActions.test.ts b/apps/web/components/booking/bookingActions.test.ts
index 14981596e7..a0ee856bc2 100644
--- a/apps/web/components/booking/bookingActions.test.ts
+++ b/apps/web/components/booking/bookingActions.test.ts
@@ -475,6 +475,34 @@ describe("Booking Actions", () => {
       expect(isActionDisabled("cancel", context)).toBe(true);
     });
 
+    it("should disable cancelling all past bookings", () => {
+      const pastConfirmedContext = createMockContext({
+        isBookingInPast: true,
+        isPending: false,
+        isConfirmed: true,
+      });
+
+      const pastPendingContext = createMockContext({
+        isBookingInPast: true,
+        isPending: true,
+        isConfirmed: false,
+      });
+
+      // Current implementation blocks ALL past bookings
+      expect(isActionDisabled("cancel", pastConfirmedContext)).toBe(true);
+      expect(isActionDisabled("cancel", pastPendingContext)).toBe(true);
+    });
+
+    it("should allow cancelling future bookings when cancelling is not disabled", () => {
+      const futureContext = createMockContext({
+        isBookingInPast: false,
+        isPending: true,
+        isConfirmed: false,
+      });
+
+      expect(isActionDisabled("cancel", futureContext)).toBe(false);
+    });
+
     it("should disable video actions for non-past bookings", () => {
       const context = createMockContext({ isBookingInPast: false });
 
diff --git a/apps/web/components/booking/bookingActions.ts b/apps/web/components/booking/bookingActions.ts
index f28647c17d..cdc6982717 100644
--- a/apps/web/components/booking/bookingActions.ts
+++ b/apps/web/components/booking/bookingActions.ts
@@ -210,7 +210,7 @@ export function isActionDisabled(actionId: string, context: BookingActionContext
     case "reschedule_request":
       return (isBookingInPast && !booking.eventType.allowReschedulingPastBookings) || isDisabledRescheduling;
     case "cancel":
-      return isDisabledCancelling || (isBookingInPast && isPending && !isConfirmed);
+      return isDisabledCancelling || isBookingInPast;
     case "view_recordings":
       return !(isBookingInPast && booking.status === BookingStatus.ACCEPTED && context.isCalVideoLocation);
     case "meeting_session_details":
diff --git a/apps/web/modules/bookings/views/bookings-single-view.tsx b/apps/web/modules/bookings/views/bookings-single-view.tsx
index 4f55f9e2a9..573a786c16 100644
--- a/apps/web/modules/bookings/views/bookings-single-view.tsx
+++ b/apps/web/modules/bookings/views/bookings-single-view.tsx
@@ -839,13 +839,13 @@ export default function Success(props: PageProps) {
                                         {t("reschedule")}
                                       </Link>
                                     </span>
-                                    {canCancelAndReschedule && (
+                                    {!isBookingInPast && canCancel && (
                                       <span className="mx-2">{t("or_lowercase")}</span>
                                     )}
                                   </span>
                                 )}
 
-                              {canCancel && (
+                              {!isBookingInPast && canCancel && (
                                 <button
                                   data-testid="cancel"
                                   className={classNames(
diff --git a/apps/web/playwright/booking-pages.e2e.ts b/apps/web/playwright/booking-pages.e2e.ts
index 2a4fb90e9f..4646d29396 100644
--- a/apps/web/playwright/booking-pages.e2e.ts
+++ b/apps/web/playwright/booking-pages.e2e.ts
@@ -766,3 +766,31 @@ test.describe("GTM container", () => {
     expect(scriptContent).toContain("googletagmanager");
   });
 });
+
+test.describe("Past booking cancellation", () => {
+  test("Cancel button should be hidden for past bookings", async ({ page, users, bookings }) => {
+    const user = await users.create({
+      name: "Test User",
+    });
+
+    await user.apiLogin();
+
+    const pastDate = new Date();
+    pastDate.setDate(pastDate.getDate() - 1);
+    const endDate = new Date(pastDate.getTime() + 30 * 60 * 1000);
+
+    const booking = await bookings.create(user.id, user.username, user.eventTypes[0].id, {
+      title: "Past Meeting",
+      startTime: pastDate,
+      endTime: endDate,
+      status: "ACCEPTED",
+    });
+
+    await page.goto("/bookings/past");
+    await page.locator('[data-testid="booking-actions-dropdown"]').nth(0).click();
+    await expect(page.locator('[data-testid="cancel"]')).toBeDisabled();
+
+    await page.goto(`/booking/${booking.uid}`);
+    await expect(page.locator('[data-testid="cancel"]')).toBeHidden();
+  });
+});
diff --git a/packages/features/bookings/lib/handleCancelBooking.ts b/packages/features/bookings/lib/handleCancelBooking.ts
index fb8038922c..d53aa7f4f1 100644
--- a/packages/features/bookings/lib/handleCancelBooking.ts
+++ b/packages/features/bookings/lib/handleCancelBooking.ts
@@ -120,6 +120,13 @@ async function handler(input: CancelBookingInput) {
     });
   }
 
+  if (bookingToDelete.endTime && new Date() > new Date(bookingToDelete.endTime)) {
+    throw new HttpError({
+      statusCode: 400,
+      message: "Cannot cancel a booking that has already ended",
+    });
+  }
+
   // If the booking is a seated event and there is no seatReferenceUid we should validate that logged in user is host
   if (bookingToDelete.eventType?.seatsPerTimeSlot && !seatReferenceUid) {
     const userIsHost = bookingToDelete.eventType.hosts.find((host) => {
diff --git a/packages/features/bookings/lib/handleCancelBooking/test/handleCancelBooking.test.ts b/packages/features/bookings/lib/handleCancelBooking/test/handleCancelBooking.test.ts
index 42214b92a3..0a349f57b8 100644
--- a/packages/features/bookings/lib/handleCancelBooking/test/handleCancelBooking.test.ts
+++ b/packages/features/bookings/lib/handleCancelBooking/test/handleCancelBooking.test.ts
@@ -420,4 +420,73 @@ describe("Cancel Booking", () => {
       },
     });
   });
+
+  test("Should block cancelling past bookings", async () => {
+    const handleCancelBooking = (await import("@calcom/features/bookings/lib/handleCancelBooking")).default;
+
+    const booker = getBooker({
+      email: "booker@example.com",
+      name: "Booker",
+    });
+
+    const organizer = getOrganizer({
+      name: "Organizer",
+      email: "organizer@example.com",
+      id: 101,
+      schedules: [TestData.schedules.IstWorkHours],
+      credentials: [getGoogleCalendarCredential()],
+      selectedCalendars: [TestData.selectedCalendars.google],
+    });
+
+    const uidOfBookingToBeCancelled = "past-booking";
+    const idOfBookingToBeCancelled = 3040;
+    const { dateString: minus1DateString } = getDate({ dateIncrement: -1 });
+
+    await createBookingScenario(
+      getScenarioData({
+        eventTypes: [
+          {
+            id: 1,
+            slotInterval: 30,
+            length: 30,
+            users: [
+              {
+                id: 101,
+              },
+            ],
+          },
+        ],
+        bookings: [
+          {
+            id: idOfBookingToBeCancelled,
+            uid: uidOfBookingToBeCancelled,
+            eventTypeId: 1,
+            userId: 101,
+            responses: {
+              email: booker.email,
+              name: booker.name,
+              location: { optionValue: "", value: BookingLocations.CalVideo },
+            },
+            status: BookingStatus.ACCEPTED,
+            startTime: `${minus1DateString}T05:00:00.000Z`,
+            endTime: `${minus1DateString}T05:30:00.000Z`,
+          },
+        ],
+        organizer,
+        apps: [TestData.apps["daily-video"]],
+      })
+    );
+
+    // This should throw an error with current implementation
+    await expect(
+      handleCancelBooking({
+        bookingData: {
+          id: idOfBookingToBeCancelled,
+          uid: uidOfBookingToBeCancelled,
+          cancelledBy: organizer.email,
+          cancellationReason: "Testing past booking cancellation",
+        },
+      })
+    ).rejects.toThrow("Cannot cancel a booking that has already ended");
+  });
 });