diff --git a/Userland/Games/Chess/ChessWidget.cpp b/Userland/Games/Chess/ChessWidget.cpp
index 3438a27545..4ce5458728 100644
--- a/Userland/Games/Chess/ChessWidget.cpp
+++ b/Userland/Games/Chess/ChessWidget.cpp
@@ -697,7 +697,7 @@ bool ChessWidget::check_game_over(ClaimDrawBehavior claim_draw_behavior)
     case Chess::Board::Result::FiftyMoveRule:
         if (claim_draw_behavior == ClaimDrawBehavior::Prompt) {
             update();
-            auto dialog_result = GUI::MessageBox::show(window(), "50 moves have elapsed without a capture. Claim Draw?"sv, "Claim Draw?"sv,
+            auto dialog_result = GUI::MessageBox::show(window(), "50 moves have elapsed without a capture or pawn advance. Claim Draw?"sv, "Claim Draw?"sv,
                 GUI::MessageBox::Type::Information, GUI::MessageBox::InputType::YesNo);
 
             if (dialog_result != GUI::Dialog::ExecResult::Yes)
diff --git a/Userland/Libraries/LibChess/Chess.cpp b/Userland/Libraries/LibChess/Chess.cpp
index 429b256bdb..ccb703bb37 100644
--- a/Userland/Libraries/LibChess/Chess.cpp
+++ b/Userland/Libraries/LibChess/Chess.cpp
@@ -774,9 +774,11 @@ Board::Result Board::game_result() const
     });
 
     if (are_legal_moves) {
-        if (m_moves_since_capture >= 75 * 2)
+        if (m_moves_since_capture >= 75 * 2 && m_moves_since_pawn_advance >= 75 * 2)
             return Result::SeventyFiveMoveRule;
-        if (m_moves_since_capture == 50 * 2)
+
+        if ((m_moves_since_capture >= 50 * 2 && m_moves_since_pawn_advance == 50 * 2)
+            || (m_moves_since_pawn_advance >= 50 * 2 && m_moves_since_capture == 50 * 2))
             return Result::FiftyMoveRule;
 
         auto repeats = m_previous_states.get(Traits<Board>::hash(*this));