diff --git a/tests/test_tinycss2.py b/tests/test_tinycss2.py
index fb1130a..c02ed72 100644
--- a/tests/test_tinycss2.py
+++ b/tests/test_tinycss2.py
@@ -703,3 +703,28 @@ def test_escape_in_function_name():
     function, = parse_component_value_list('\\dddf()')
     assert function.type == 'function'
     assert function.name == '\udddf'
+
+
+@pytest.mark.parametrize('source', [
+    '1 %',       # number + '%'   would merge into a percentage
+    '1.5 %',     # (float) number + '%'
+    '+1 %',      # (signed) number + '%'
+    '1 -->',     # number + CDC    '--' would extend the number's unit
+    '# -',       # '#' + '-'       would merge into a hash token
+    '# -->',     # '#' + CDC
+    '- -',       # '-' + '-'       would merge into an ident '--'
+    '- -->',     # '-' + CDC
+    '@ -->',     # '@' + CDC       would merge into an at-keyword
+])
+def test_serialize_adjacent_tokens_do_not_merge(source):
+    # A pair of tokens separated only by whitespace must survive a round trip
+    # even once that whitespace is dropped (e.g. by a minifier): serialize()
+    # has to insert a separator, otherwise the two tokens re-parse as one.
+    # These pairs are listed in the CSS Syntax serialization table but were
+    # missing from BAD_PAIRS. See https://drafts.csswg.org/css-syntax/#serialization
+    tokens = parse_component_value_list(source)
+    del tokens[1]  # drop the whitespace token between the two component values
+    reparsed = parse_component_value_list(serialize(tokens))
+    reparsed = [t for t in reparsed if t.type not in ('whitespace', 'comment')]
+    assert [t.type for t in reparsed] == [t.type for t in tokens]
+    assert [t.serialize() for t in reparsed] == [t.serialize() for t in tokens]
diff --git a/tinycss2/serializer.py b/tinycss2/serializer.py
index 032b924..a1c5338 100644
--- a/tinycss2/serializer.py
+++ b/tinycss2/serializer.py
@@ -133,6 +133,15 @@ def _serialize_to(nodes, write):
     [(a, b)
         for a in ('ident', 'at-keyword', 'hash', 'dimension')
         for b in ('-', '-->')] +
+    # Per the CSS Syntax serialization table, a lone U+002D HYPHEN-MINUS
+    # delimiter also merges after '#'/'-' (forming a hash or ident), and a CDC
+    # ('-->') merges after '#'/'-'/number/'@' (its leading '--' is consumed as
+    # hash/ident/dimension-unit/at-keyword characters). A '%' delimiter merges
+    # into a preceding number to form a percentage.
+    # https://drafts.csswg.org/css-syntax/#serialization
+    [(a, '-') for a in ('#', '-')] +
+    [(a, '-->') for a in ('#', '-', 'number', '@')] +
+    [('number', '%')] +
     [(a, b)
         for a in ('#', '-', 'number', '@')
         for b in ('ident', 'function', 'url')] +