diff --git a/openapi-request-validator-core/src/main/java/com/atlassian/oai/validator/model/ApiPathImpl.java b/openapi-request-validator-core/src/main/java/com/atlassian/oai/validator/model/ApiPathImpl.java
index 372e589d..1acd36f4 100644
--- a/openapi-request-validator-core/src/main/java/com/atlassian/oai/validator/model/ApiPathImpl.java
+++ b/openapi-request-validator-core/src/main/java/com/atlassian/oai/validator/model/ApiPathImpl.java
@@ -33,6 +33,9 @@ public class ApiPathImpl extends NormalisedPathImpl implements ApiPath {
 
     private final boolean strictPathMatching;
 
+    /** Compiled once per part - the path template is fixed for the lifetime of this instance. */
+    private final Pattern[] partPatterns;
+
     public ApiPathImpl(@Nonnull final String path, @Nullable final String apiPrefix) {
         this(path, apiPrefix, false);
     }
@@ -45,6 +48,10 @@ public ApiPathImpl(@Nonnull final String path,
                        final boolean strictPathMatching) {
         super(path, apiPrefix);
         this.strictPathMatching = strictPathMatching;
+        this.partPatterns = new Pattern[numberOfParts()];
+        for (int i = 0; i < partPatterns.length; i++) {
+            partPatterns[i] = compile(quote(part(i)).replaceAll(PARAM_REGEX, "\\\\E(.*?)\\\\Q"), CASE_INSENSITIVE);
+        }
     }
 
     @Override
@@ -66,9 +73,7 @@ public boolean matches(final NormalisedPath requestPath) {
     @Override
     public boolean partMatches(final int index, @Nonnull final String requestPathPart) {
         requireNonNull(requestPathPart, "A request path part is required");
-        final String template = part(index);
-        final Pattern templatePattern = compile(quote(template).replaceAll(PARAM_REGEX, "\\\\E(.*?)\\\\Q"), CASE_INSENSITIVE);
-        return templatePattern.matcher(requestPathPart).matches();
+        return partPatterns[index].matcher(requestPathPart).matches();
     }
 
     @Override
diff --git a/openapi-request-validator-core/src/test/java/com/atlassian/oai/validator/model/ApiPathImplTest.java b/openapi-request-validator-core/src/test/java/com/atlassian/oai/validator/model/ApiPathImplTest.java
index fc968557..705dfa8f 100644
--- a/openapi-request-validator-core/src/test/java/com/atlassian/oai/validator/model/ApiPathImplTest.java
+++ b/openapi-request-validator-core/src/test/java/com/atlassian/oai/validator/model/ApiPathImplTest.java
@@ -10,6 +10,7 @@
 import static org.hamcrest.Matchers.containsInAnyOrder;
 import static org.hamcrest.Matchers.empty;
 import static org.hamcrest.Matchers.is;
+import static org.junit.jupiter.api.Assertions.assertThrows;
 
 public class ApiPathImplTest {
 
@@ -212,6 +213,44 @@ public void matches_doesNotMatches_whenBadParamMatch() {
         assertThat(matches("/p1/p2/{param1}-{param2}", "/p1/p2/floop"), is(false));
     }
 
+    @Test
+    public void partMatches_matchesLiterally_whenPartContainsRegexMetacharacters() {
+        assertThat(partMatches("a.b", "a.b"), is(true));
+        assertThat(partMatches("a.b", "axb"), is(false));
+        assertThat(partMatches("a+b", "a+b"), is(true));
+        assertThat(partMatches("a+b", "aab"), is(false));
+    }
+
+    @Test
+    public void partMatches_throws_whenIndexOutOfRange() {
+        final ApiPathImpl classUnderTest = new ApiPathImpl("/{id}", null);
+
+        assertThrows(IndexOutOfBoundsException.class, () -> classUnderTest.partMatches(1, "foop"));
+    }
+
+    @Test
+    public void partMatches_isRepeatable_onTheSameInstance() {
+        final ApiPathImpl classUnderTest = new ApiPathImpl("/{id}/literal/a.b/a+b", null);
+
+        assertThat(classUnderTest.partMatches(0, "foop"), is(true));
+        assertThat(classUnderTest.partMatches(1, "literal"), is(true));
+        assertThat(classUnderTest.partMatches(1, "LITERAL"), is(true));
+        assertThat(classUnderTest.partMatches(1, "blarp"), is(false));
+        assertThat(classUnderTest.partMatches(2, "a.b"), is(true));
+        assertThat(classUnderTest.partMatches(2, "axb"), is(false));
+        assertThat(classUnderTest.partMatches(3, "a+b"), is(true));
+        assertThat(classUnderTest.partMatches(3, "aab"), is(false));
+    }
+
+    @Test
+    public void matches_isRepeatable_onTheSameInstance() {
+        final ApiPathImpl classUnderTest = new ApiPathImpl("/p1/{param1}/p3", null);
+
+        assertThat(classUnderTest.matches(new NormalisedPathImpl("/p1/foop/p3", null)), is(true));
+        assertThat(classUnderTest.matches(new NormalisedPathImpl("/p1/foop/P3", null)), is(true));
+        assertThat(classUnderTest.matches(new NormalisedPathImpl("/p1/foop/blarp", null)), is(false));
+    }
+
     private static void testParamValueExtraction(final String expression, final String path, final String... expected) {
         assertThat(new ApiPathImpl(expression, null).paramValues(0, path).values(),
                 containsInAnyOrder(stream(expected).map(e -> is(ofNullable(e))).collect(toList())));