diff --git a/apps/web/components/booking/BookingListItem.tsx b/apps/web/components/booking/BookingListItem.tsx
index 1aa309e2e8..65601e410e 100644
--- a/apps/web/components/booking/BookingListItem.tsx
+++ b/apps/web/components/booking/BookingListItem.tsx
@@ -387,10 +387,14 @@ function BookingListItem(booking: BookingItemProps) {
     );
   };
 
+  const bookingYear = dayjs(booking.startTime).year();
+  const currentYear = dayjs().year();
+  const isDifferentYear = bookingYear !== currentYear;
+
   const startTime = dayjs(booking.startTime)
     .tz(userTimeZone)
     .locale(language)
-    .format(isUpcoming ? "ddd, D MMM" : "D MMMM YYYY");
+    .format(isUpcoming ? (isDifferentYear ? "ddd, D MMM YYYY" : "ddd, D MMM") : "D MMMM YYYY");
   const [isOpenRescheduleDialog, setIsOpenRescheduleDialog] = useState(false);
   const [isOpenReassignDialog, setIsOpenReassignDialog] = useState(false);
   const [isOpenSetLocationDialog, setIsOpenLocationDialog] = useState(false);