diff --git a/Libraries/LibWeb/HTML/HTMLLinkElement.cpp b/Libraries/LibWeb/HTML/HTMLLinkElement.cpp
index 381820a5622..d5242517c4c 100644
--- a/Libraries/LibWeb/HTML/HTMLLinkElement.cpp
+++ b/Libraries/LibWeb/HTML/HTMLLinkElement.cpp
@@ -56,7 +56,14 @@ void HTMLLinkElement::removed_from(Node* old_parent, Node& old_root)
 {
     Base::removed_from(old_parent, old_root);
     if (m_loaded_style_sheet) {
-        document_or_shadow_root_style_sheets().remove_a_css_style_sheet(*m_loaded_style_sheet);
+        auto& style_sheet_list = [&old_root] -> CSS::StyleSheetList& {
+            if (auto* shadow_root = as_if<DOM::ShadowRoot>(old_root); shadow_root)
+                return shadow_root->style_sheets();
+
+            return as<DOM::Document>(old_root).style_sheets();
+        }();
+
+        style_sheet_list.remove_a_css_style_sheet(*m_loaded_style_sheet);
         m_loaded_style_sheet = nullptr;
     }
 }
@@ -487,7 +494,7 @@ void HTMLLinkElement::process_stylesheet_resource(bool success, Fetch::Infrastru
                     if (!response.url_list().is_empty())
                         location = response.url_list().first().to_string();
 
-                    document().style_sheets().create_a_css_style_sheet(
+                    document_or_shadow_root_style_sheets().create_a_css_style_sheet(
                         "text/css"_string,
                         this,
                         attribute(HTML::AttributeNames::media).value_or({}),
diff --git a/Tests/LibWeb/Text/expected/HTML/HTMLLinkElement-appends-and-removes-from-ShadowRoot-styleSheets.txt b/Tests/LibWeb/Text/expected/HTML/HTMLLinkElement-appends-and-removes-from-ShadowRoot-styleSheets.txt
new file mode 100644
index 00000000000..7184d2c3889
--- /dev/null
+++ b/Tests/LibWeb/Text/expected/HTML/HTMLLinkElement-appends-and-removes-from-ShadowRoot-styleSheets.txt
@@ -0,0 +1,13 @@
+== before appending
+is linkEl.sheet null? true
+- document stylesheets (length = 0)
+- shadow root stylesheets (length = 0)
+== link loaded
+is linkEl.sheet null? false
+- document stylesheets (length = 0)
+- shadow root stylesheets (length = 1)
+-- shadow root linkEl.sheet === sheet: true
+== link removed
+is linkEl.sheet null? true
+- document stylesheets (length = 0)
+- shadow root stylesheets (length = 0)
diff --git a/Tests/LibWeb/Text/input/HTML/HTMLLinkElement-appends-and-removes-from-ShadowRoot-styleSheets.html b/Tests/LibWeb/Text/input/HTML/HTMLLinkElement-appends-and-removes-from-ShadowRoot-styleSheets.html
new file mode 100644
index 00000000000..ef290e73986
--- /dev/null
+++ b/Tests/LibWeb/Text/input/HTML/HTMLLinkElement-appends-and-removes-from-ShadowRoot-styleSheets.html
@@ -0,0 +1,40 @@
+<!DOCTYPE html>
+<div id="shadowhost"></div>
+<script src="../include.js"></script>
+<script>
+    asyncTest((done) => {
+        const shadowHost = document.getElementById("shadowhost");
+        const shadowRoot = shadowHost.attachShadow({ mode: "closed" });
+
+        const linkEl = document.createElement("link");
+        linkEl.href = "../valid.css";
+        linkEl.rel = "stylesheet";
+
+        const printSheets = () => {
+            println(`is linkEl.sheet null? ${linkEl.sheet === null}`)
+            println(`- document stylesheets (length = ${document.styleSheets.length})`);
+            for (const sheet of document.styleSheets) {
+                println(`-- document stylesheet linkEl.sheet === sheet: ${linkEl.sheet === sheet}`);
+            }
+            println(`- shadow root stylesheets (length = ${shadowRoot.styleSheets.length})`);
+            for (const sheet of shadowRoot.styleSheets) {
+                println(`-- shadow root linkEl.sheet === sheet: ${linkEl.sheet === sheet}`);
+            }
+        };
+
+        println("== before appending");
+        printSheets();
+
+        linkEl.addEventListener("load", () => {
+            println("== link loaded");
+            printSheets();
+
+            linkEl.remove();
+            println("== link removed");
+            printSheets();
+            done();
+        }, { once: true });
+
+        shadowRoot.appendChild(linkEl);
+    });
+</script>
