diff --git a/aiohttp/connector.py b/aiohttp/connector.py
index 5e47ce597ab..99f319824e6 100644
--- a/aiohttp/connector.py
+++ b/aiohttp/connector.py
@@ -161,15 +161,21 @@ def _cleanup(self):
         now = self._loop.time()
 
         connections = {}
+        timeout = self._keepalive_timeout
+
         for key, conns in self._conns.items():
             alive = []
             for transport, proto, t0 in conns:
                 if transport is not None:
                     if proto and not proto.is_connected():
                         transport = None
-                    elif (now - t0) > self._keepalive_timeout:
-                        transport.close()
-                        transport = None
+                    else:
+                        delta = t0 + self._keepalive_timeout - now
+                        if delta < 0:
+                            transport.close()
+                            transport = None
+                        elif delta < timeout:
+                            timeout = delta
 
                 if transport is not None:
                     alive.append((transport, proto, t0))
@@ -178,7 +184,7 @@ def _cleanup(self):
 
         if connections:
             self._cleanup_handle = self._loop.call_at(
-                ceil(now + self._keepalive_timeout), self._cleanup)
+                ceil(now + timeout), self._cleanup)
 
         self._conns = connections
 
diff --git a/tests/test_connector.py b/tests/test_connector.py
index 7a6380d5507..061bbeafafa 100644
--- a/tests/test_connector.py
+++ b/tests/test_connector.py
@@ -417,7 +417,26 @@ def test_cleanup2(self):
 
         self.assertIsNotNone(conn._cleanup_handle)
         loop.call_at.assert_called_with(
-            311, conn._cleanup)
+            310, conn._cleanup)
+        conn.close()
+
+    def test_cleanup3(self):
+        testset = {1: [(unittest.mock.Mock(), unittest.mock.Mock(), 290.1),
+                       (unittest.mock.Mock(), unittest.mock.Mock(), 305.1)]}
+        testset[1][0][1].is_connected.return_value = True
+
+        loop = unittest.mock.Mock()
+        loop.time.return_value = 308.5
+
+        conn = aiohttp.BaseConnector(loop=loop, keepalive_timeout=10)
+        conn._conns = testset
+
+        conn._cleanup()
+        self.assertEqual(conn._conns, {1: [testset[1][1]]})
+
+        self.assertIsNotNone(conn._cleanup_handle)
+        loop.call_at.assert_called_with(
+            316, conn._cleanup)
         conn.close()
 
     def test_tcp_connector_ctor(self):