diff --git a/src/Parser/InlineParser.php b/src/Parser/InlineParser.php
index 56413a4..affa6fa 100644
--- a/src/Parser/InlineParser.php
+++ b/src/Parser/InlineParser.php
@@ -1369,74 +1369,6 @@ protected function parseSmartQuote(string $text, int $pos, string $quote): strin
         return $this->closeSingleQuote;
     }
 
-    /**
-     * Find a matching single quote closer for a potential opener at $pos
-     *
-     * Returns the position of the closer if found, null otherwise.
-     * Uses a matching algorithm similar to emphasis - potential openers and closers
-     * are matched from innermost pairs outward.
-     */
-    protected function findMatchingSingleQuoteCloser(string $text, int $openerPos): ?int
-    {
-        $length = strlen($text);
-
-        // Collect all potential openers and closers after this position
-        $openers = [$openerPos];
-        $closers = [];
-
-        for ($i = $openerPos + 1; $i < $length; $i++) {
-            if ($text[$i] !== "'") {
-                continue;
-            }
-
-            $prevChar = $text[$i - 1] ?? ' ';
-            $nextChar = $text[$i + 1] ?? ' ';
-            $prevIsSpace = ctype_space($prevChar);
-            // Closer can be followed by space, punctuation, or end of string
-            $nextIsSpaceOrPunct = ctype_space($nextChar) || $i === $length - 1
-                || preg_match('/^[\p{P}\p{S}]/u', $nextChar);
-
-            // Skip quotes before digits (always apostrophe)
-            if (ctype_digit($nextChar)) {
-                continue;
-            }
-
-            // Skip quotes after ] or )
-            if ($prevChar === ']' || $prevChar === ')') {
-                continue;
-            }
-
-            $nextIsSpace = ctype_space($nextChar);
-            if ($prevIsSpace && !$nextIsSpace) {
-                // Could be opener (after space, before non-space)
-                $openers[] = $i;
-            } elseif (!$prevIsSpace && $nextIsSpaceOrPunct) {
-                // Could be closer (after non-space, before space/punct)
-                $closers[] = $i;
-            } elseif (!$prevIsSpace) {
-                // Mid-word quote (like Jane's) - typically apostrophe
-                continue;
-            }
-        }
-
-        // Now match openers with closers, innermost first
-        // For each closer, find the nearest preceding unmatched opener
-        $matched = [];
-        foreach ($closers as $closer) {
-            for ($j = count($openers) - 1; $j >= 0; $j--) {
-                $opener = $openers[$j];
-                if ($opener < $closer && !isset($matched[$opener])) {
-                    $matched[$opener] = $closer;
-
-                    break;
-                }
-            }
-        }
-
-        // Return the closer for our position, if any
-        return $matched[$openerPos] ?? null;
-    }
-
     /**
      * Build a cache of all single quote opener→closer matches for the text.
      *
@@ -1453,10 +1385,14 @@ protected function buildSingleQuoteMatchCache(string $text): array
         }
 
         $length = strlen($text);
-        $openers = [];
-        $closers = [];
+        $matched = [];
+        $openerStack = [];
 
-        // Single pass: collect all potential openers and closers
+        // Single forward pass: classify each quote and pair a closer with the
+        // innermost still-open opener via a stack. The stack top is always the
+        // largest-index unmatched opener seen so far, so popping it reproduces
+        // the former "nearest preceding unmatched opener" pairing in O(n)
+        // instead of the previous O(n²) closer-by-opener scan.
         for ($i = 0; $i < $length; $i++) {
             if ($text[$i] !== "'") {
                 continue;
@@ -1493,28 +1429,15 @@ protected function buildSingleQuoteMatchCache(string $text): array
             }
 
             if ($prevIsSpace && !$nextIsSpace) {
-                // Potential opener
-                $openers[] = $i;
-            } elseif (!$prevIsSpace && $nextIsSpaceOrPunct) {
-                // Potential closer
-                $closers[] = $i;
+                // Potential opener - push onto the stack of open quotes
+                $openerStack[] = $i;
+            } elseif (!$prevIsSpace && $nextIsSpaceOrPunct && $openerStack) {
+                // Potential closer - pair with the innermost unmatched opener
+                $matched[array_pop($openerStack)] = $i;
             }
             // Mid-word quotes are skipped (apostrophes)
         }
 
-        // Match openers with closers, innermost first
-        $matched = [];
-        foreach ($closers as $closer) {
-            for ($j = count($openers) - 1; $j >= 0; $j--) {
-                $opener = $openers[$j];
-                if ($opener < $closer && !isset($matched[$opener])) {
-                    $matched[$opener] = $closer;
-
-                    break;
-                }
-            }
-        }
-
         return $matched;
     }
 
diff --git a/tests/TestCase/Parser/SingleQuoteMatchingTest.php b/tests/TestCase/Parser/SingleQuoteMatchingTest.php
new file mode 100644
index 0000000..2c82f91
--- /dev/null
+++ b/tests/TestCase/Parser/SingleQuoteMatchingTest.php
@@ -0,0 +1,42 @@
+<?php
+
+declare(strict_types=1);
+
+namespace Djot\Test\TestCase\Parser;
+
+use Djot\DjotConverter;
+use PHPUnit\Framework\Attributes\DataProvider;
+use PHPUnit\Framework\TestCase;
+
+/**
+ * Locks the single-quote opener/closer pairing produced by
+ * InlineParser::buildSingleQuoteMatchCache(), so the O(n) stack-based
+ * matching keeps the exact behavior of the former O(n^2) scan.
+ */
+class SingleQuoteMatchingTest extends TestCase
+{
+    /**
+     * @return array<string, array{0: string, 1: string}>
+     */
+    public static function quoteProvider(): array
+    {
+        return [
+            // A balanced pair becomes an open + close curly quote.
+            'matched pair' => ["'hello'", "\u{2018}hello\u{2019}"],
+            // A flanking opener with no later closer stays an apostrophe.
+            'lone opener is apostrophe' => ['say \'what', "say \u{2019}what"],
+            // Nested pairs match innermost-first (inner pair closes before outer).
+            'nested pairs' => ["'a 'b' c'", "\u{2018}a \u{2018}b\u{2019} c\u{2019}"],
+            // Mid-word apostrophe is untouched; the following pair still matches.
+            'apostrophe then pair' => ["it's a 'test'", "it\u{2019}s a \u{2018}test\u{2019}"],
+        ];
+    }
+
+    #[DataProvider('quoteProvider')]
+    public function testSingleQuotePairing(string $input, string $expected): void
+    {
+        $html = (new DjotConverter())->convert($input);
+
+        $this->assertStringContainsString($expected, $html);
+    }
+}