diff --git a/playhouse/pool.py b/playhouse/pool.py
index 62caece1a..d5a35eacf 100644
--- a/playhouse/pool.py
+++ b/playhouse/pool.py
@@ -34,7 +34,6 @@ class Meta:
 import functools
 import heapq
 import logging
-import random
 import threading
 import time
 from collections import namedtuple
@@ -68,6 +67,10 @@ class MaxConnectionsExceeded(ValueError): pass
 PoolConnection = namedtuple('PoolConnection', ('timestamp', 'connection',
                                                'checked_out'))
 
+class _sentinel(object):
+    def __lt__(self, other):
+        return True
+
 
 def locked(fn):
     @functools.wraps(fn)
@@ -136,7 +139,8 @@ def _connect(self):
         while True:
             try:
                 # Remove the oldest connection from the heap.
-                ts, conn = heapq.heappop(self._connections)
+                ts, _, c_conn = heapq.heappop(self._connections)
+                conn = c_conn
                 key = self.conn_key(conn)
             except IndexError:
                 ts = conn = None
@@ -167,7 +171,7 @@ def _connect(self):
                     len(self._in_use) >= self._max_connections):
                 raise MaxConnectionsExceeded('Exceeded maximum connections.')
             conn = super(PooledDatabase, self)._connect()
-            ts = time.time() - random.random() / 1000
+            ts = time.time()
             key = self.conn_key(conn)
             logger.debug('Created new connection %s.', key)
 
@@ -198,7 +202,8 @@ def _close(self, conn, close_conn=False):
                 super(PooledDatabase, self)._close(conn)
             elif self._can_reuse(conn):
                 logger.debug('Returning %s to pool.', key)
-                heapq.heappush(self._connections, (pool_conn.timestamp, conn))
+                heapq.heappush(self._connections,
+                               (pool_conn.timestamp, _sentinel(), conn))
             else:
                 logger.debug('Closed %s.', key)
 
@@ -224,7 +229,7 @@ def manual_close(self):
     @locked
     def close_idle(self):
         # Close any open connections that are not currently in-use.
-        for _, conn in self._connections:
+        for _, _, conn in self._connections:
             self._close(conn, close_conn=True)
         self._connections = []
 
@@ -249,7 +254,7 @@ def close_all(self):
         # Close all connections -- available and in-use. Warning: may break any
         # active connections used by other threads.
         self.close()
-        for _, conn in self._connections:
+        for _, _, conn in self._connections:
             self._close(conn, close_conn=True)
         for pool_conn in self._in_use.values():
             self._close(pool_conn.connection, close_conn=True)
diff --git a/tests/pool.py b/tests/pool.py
index 319afcdb0..cb5d16b20 100644
--- a/tests/pool.py
+++ b/tests/pool.py
@@ -112,7 +112,7 @@ def open_conn():
 
         self.assertEqual(db.counter, 5)
         self.assertEqual(
-            sorted([conn for _, conn in db._connections]),
+            sorted([conn for _, _, conn in db._connections]),
             [1, 2, 3, 4, 5])  # All 5 are ready to be re-used.
         self.assertEqual(db._in_use, {})
 
@@ -184,9 +184,9 @@ def test_close_idle(self):
         db = FakePooledDatabase('testing', counter=3)
 
         now = time.time()
-        heapq.heappush(db._connections, (now - 10, 3))
-        heapq.heappush(db._connections, (now - 5, 2))
-        heapq.heappush(db._connections, (now - 1, 1))
+        heapq.heappush(db._connections, (now - 10, None, 3))
+        heapq.heappush(db._connections, (now - 5, None, 2))
+        heapq.heappush(db._connections, (now - 1, None, 1))
 
         self.assertEqual(db.connection(), 3)
         self.assertTrue(3 in db._in_use)
@@ -218,9 +218,9 @@ def test_close_all(self):
         db = FakePooledDatabase('testing', counter=3)
 
         now = time.time()
-        heapq.heappush(db._connections, (now - 10, 3))
-        heapq.heappush(db._connections, (now - 5, 2))
-        heapq.heappush(db._connections, (now - 1, 1))
+        heapq.heappush(db._connections, (now - 10, None, 3))
+        heapq.heappush(db._connections, (now - 5, None, 2))
+        heapq.heappush(db._connections, (now - 1, None, 1))
         self.assertEqual(db.connection(), 3)
         self.assertTrue(3 in db._in_use)
 
@@ -234,10 +234,10 @@ def test_stale_timeout_cascade(self):
         now = time.time()
         db = FakePooledDatabase('testing', stale_timeout=10)
         conns = [
-            (now - 20, 1),
-            (now - 15, 2),
-            (now - 5, 3),
-            (now, 4),
+            (now - 20, None, 1),
+            (now - 15, None, 2),
+            (now - 5, None, 3),
+            (now, None, 4),
         ]
         for ts_conn in conns:
             heapq.heappush(db._connections, ts_conn)
@@ -245,7 +245,7 @@ def test_stale_timeout_cascade(self):
         self.assertEqual(db.connection(), 3)
         self.assertEqual(len(db._in_use), 1)
         self.assertTrue(3 in db._in_use)
-        self.assertEqual(db._connections, [(now, 4)])
+        self.assertEqual(db._connections, [(now, None, 4)])
 
     def test_connect_cascade(self):
         now = time.time()
@@ -256,10 +256,10 @@ def _is_closed(self, conn):
         db = ClosedPooledDatabase('testing', stale_timeout=10)
 
         conns = [
-            (now - 15, 1),  # Skipped due to being stale.
-            (now - 5, 2),  # Will appear closed.
-            (now - 3, 3),
-            (now, 4),  # Will appear closed.
+            (now - 15, None, 1),  # Skipped due to being stale.
+            (now - 5, None, 2),  # Will appear closed.
+            (now - 3, None, 3),
+            (now, None, 4),  # Will appear closed.
         ]
         db.counter = 4  # The next connection we create will have id=5.
         for ts_conn in conns:
@@ -272,7 +272,7 @@ def _is_closed(self, conn):
         pool_conn = db._in_use[3]
         self.assertEqual(pool_conn.timestamp, now - 3)
         self.assertEqual(pool_conn.connection, 3)
-        self.assertEqual(db._connections, [(now, 4)])
+        self.assertEqual(db._connections, [(now, None, 4)])
 
         # Since conn 4 is closed, we will open a new conn.
         db._state.closed = True  # Pretend we're in a different thread.