diff --git a/commonTestResources/exampleOpenApiFiles/valid/preferLeastTemplatedPathOverMostTemplatedPath/leastTemplatedPathAfterMostTemplatedPath/openapi2.yml b/commonTestResources/exampleOpenApiFiles/valid/preferLeastTemplatedPathOverMostTemplatedPath/leastTemplatedPathAfterMostTemplatedPath/openapi2.yml
new file mode 100644
index 00000000..479f9a35
--- /dev/null
+++ b/commonTestResources/exampleOpenApiFiles/valid/preferLeastTemplatedPathOverMostTemplatedPath/leastTemplatedPathAfterMostTemplatedPath/openapi2.yml
@@ -0,0 +1,20 @@
+swagger: '2.0'
+info:
+  title: Test OpenApi 2 spec
+  description: Test that our plugins prefer to match responses to least-templated paths over most-templated paths
+  version: 0.1.0
+paths:
+  ? '/preferLeastTemplatedPathOverMostTemplatedPath/{templatedPath}/{templatedPath2}'
+  : get:
+      responses:
+        200:
+          description: Response body should be a number
+          schema:
+            type: number
+  ? '/preferLeastTemplatedPathOverMostTemplatedPath/{templatedPath}/nonTemplatedPath'
+  : get:
+      responses:
+        200:
+          description: Response body should be a string
+          schema:
+            type: string
diff --git a/commonTestResources/exampleOpenApiFiles/valid/preferLeastTemplatedPathOverMostTemplatedPath/leastTemplatedPathAfterMostTemplatedPath/openapi3.yml b/commonTestResources/exampleOpenApiFiles/valid/preferLeastTemplatedPathOverMostTemplatedPath/leastTemplatedPathAfterMostTemplatedPath/openapi3.yml
new file mode 100644
index 00000000..1e8fb6e4
--- /dev/null
+++ b/commonTestResources/exampleOpenApiFiles/valid/preferLeastTemplatedPathOverMostTemplatedPath/leastTemplatedPathAfterMostTemplatedPath/openapi3.yml
@@ -0,0 +1,24 @@
+openapi: 3.0.0
+info:
+  title: Test OpenApi 3 spec
+  description: Test that our plugins prefer to match responses to least-templated paths over most-templated paths
+  version: 0.1.0
+paths:
+  ? /preferLeastTemplatedPathOverMostTemplatedPath/{templatedPath}/{templatedPath2}
+  : get:
+      responses:
+        200:
+          description: Response body should be a number
+          content:
+            application/json:
+              schema:
+                type: number
+  ? /preferLeastTemplatedPathOverMostTemplatedPath/{templatedPath}/nonTemplatedPath
+  : get:
+      responses:
+        200:
+          description: Response body should be a string
+          content:
+            application/json:
+              schema:
+                type: string
diff --git a/commonTestResources/exampleOpenApiFiles/valid/preferLeastTemplatedPathOverMostTemplatedPath/leastTemplatedPathBeforeMostTemplatedPath/openapi2.yml b/commonTestResources/exampleOpenApiFiles/valid/preferLeastTemplatedPathOverMostTemplatedPath/leastTemplatedPathBeforeMostTemplatedPath/openapi2.yml
new file mode 100644
index 00000000..e159173a
--- /dev/null
+++ b/commonTestResources/exampleOpenApiFiles/valid/preferLeastTemplatedPathOverMostTemplatedPath/leastTemplatedPathBeforeMostTemplatedPath/openapi2.yml
@@ -0,0 +1,20 @@
+swagger: '2.0'
+info:
+  title: Test OpenApi 2 spec
+  description: Test that our plugins prefer to match responses to least-templated paths over most-templated paths
+  version: 0.1.0
+paths:
+  ? /preferLeastTemplatedPathOverMostTemplatedPath/{templatedPath}/nonTemplatedPath
+  : get:
+      responses:
+        200:
+          description: Response body should be a string
+          schema:
+            type: string
+  ? /preferLeastTemplatedPathOverMostTemplatedPath/{templatedPath}/{templatedPath2}
+  : get:
+      responses:
+        200:
+          description: Response body should be a number
+          schema:
+            type: number
diff --git a/commonTestResources/exampleOpenApiFiles/valid/preferLeastTemplatedPathOverMostTemplatedPath/leastTemplatedPathBeforeMostTemplatedPath/openapi3.yml b/commonTestResources/exampleOpenApiFiles/valid/preferLeastTemplatedPathOverMostTemplatedPath/leastTemplatedPathBeforeMostTemplatedPath/openapi3.yml
new file mode 100644
index 00000000..b9157e58
--- /dev/null
+++ b/commonTestResources/exampleOpenApiFiles/valid/preferLeastTemplatedPathOverMostTemplatedPath/leastTemplatedPathBeforeMostTemplatedPath/openapi3.yml
@@ -0,0 +1,24 @@
+openapi: 3.0.0
+info:
+  title: Test OpenApi 3 spec
+  description: Test that our plugins prefer to match responses to least-templated paths over most-templated paths
+  version: 0.1.0
+paths:
+  ? /preferLeastTemplatedPathOverMostTemplatedPath/{templatedPath}/nonTemplatedPath
+  : get:
+      responses:
+        200:
+          description: Response body should be a string
+          content:
+            application/json:
+              schema:
+                type: string
+  ? /preferLeastTemplatedPathOverMostTemplatedPath/{templatedPath}/{templatedPath2}
+  : get:
+      responses:
+        200:
+          description: Response body should be a number
+          content:
+            application/json:
+              schema:
+                type: number
diff --git a/packages/chai-openapi-response-validator/test/assertions/satisfyApiSpec/preferLeastTemplatedPathOverMostTemplatedPath.test.ts b/packages/chai-openapi-response-validator/test/assertions/satisfyApiSpec/preferLeastTemplatedPathOverMostTemplatedPath.test.ts
new file mode 100644
index 00000000..3374744e
--- /dev/null
+++ b/packages/chai-openapi-response-validator/test/assertions/satisfyApiSpec/preferLeastTemplatedPathOverMostTemplatedPath.test.ts
@@ -0,0 +1,67 @@
+import chai from 'chai';
+import path from 'path';
+
+import chaiResponseValidator from '../../..';
+
+const openApiSpecsDir = path.resolve(
+  '../../commonTestResources/exampleOpenApiFiles/valid/preferLeastTemplatedPathOverMostTemplatedPath',
+);
+const { expect } = chai;
+
+describe('expect(res).to.satisfyApiSpec (using an OpenAPI spec with similar least-templated and most-templated OpenAPI paths)', () => {
+  [2, 3].forEach((openApiVersion) => {
+    describe(`OpenAPI ${openApiVersion}`, () => {
+      const openApiSpecs = [
+        {
+          isLeastTemplatedPathFirst: true,
+          pathToApiSpec: path.join(
+            openApiSpecsDir,
+            'leastTemplatedPathBeforeMostTemplatedPath',
+            `openapi${openApiVersion}.yml`,
+          ),
+        },
+        {
+          isLeastTemplatedPathFirst: false,
+          pathToApiSpec: path.join(
+            openApiSpecsDir,
+            'leastTemplatedPathAfterMostTemplatedPath',
+            `openapi${openApiVersion}.yml`,
+          ),
+        },
+      ];
+
+      openApiSpecs.forEach((spec) => {
+        const { pathToApiSpec, isLeastTemplatedPathFirst } = spec;
+
+        describe(`res.req.path matches a least-templated OpenAPI path ${
+          isLeastTemplatedPathFirst ? 'before' : 'after'
+        } a templated OpenAPI path`, () => {
+          const res = {
+            status: 200,
+            req: {
+              method: 'GET',
+              path:
+                '/preferLeastTemplatedPathOverMostTemplatedPath/templatedPath/nonTemplatedPath',
+            },
+            body: 'valid body (string)',
+          };
+
+          before(() => {
+            chai.use(chaiResponseValidator(pathToApiSpec));
+          });
+
+          it('passes', () => {
+            expect(res).to.satisfyApiSpec;
+          });
+
+          it('fails when using .not', () => {
+            const assertion = () => expect(res).to.not.satisfyApiSpec;
+            expect(assertion).to.throw(
+              "not to satisfy the '200' response defined for endpoint 'GET /preferLeastTemplatedPathOverMostTemplatedPath/{templatedPath}/nonTemplatedPath'",
+            );
+          });
+        });
+      });
+    });
+  });
+});
diff --git a/packages/jest-openapi/__test__/matchers/toSatisfyApiSpec/preferLeastTemplatedPathOverMostTemplatedPath.test.ts b/packages/jest-openapi/__test__/matchers/toSatisfyApiSpec/preferLeastTemplatedPathOverMostTemplatedPath.test.ts
new file mode 100644
index 00000000..ccc0bd93
--- /dev/null
+++ b/packages/jest-openapi/__test__/matchers/toSatisfyApiSpec/preferLeastTemplatedPathOverMostTemplatedPath.test.ts
@@ -0,0 +1,65 @@
+import path from 'path';
+
+import jestOpenAPI from '../../..';
+
+const openApiSpecsDir = path.resolve(
+  '../../commonTestResources/exampleOpenApiFiles/valid/preferLeastTemplatedPathOverMostTemplatedPath',
+);
+
+describe('expect(res).toSatisfyApiSpec() (using an OpenAPI spec with similar templated and non-templated OpenAPI paths)', () => {
+  [2, 3].forEach((openApiVersion) => {
+    describe(`OpenAPI ${openApiVersion}`, () => {
+      const openApiSpecs = [
+        {
+          isLeastTemplatedPathFirst: true,
+          pathToApiSpec: path.join(
+            openApiSpecsDir,
+            'leastTemplatedPathBeforeMostTemplatedPath',
+            `openapi${openApiVersion}.yml`,
+          ),
+        },
+        {
+          isLeastTemplatedPathFirst: false,
+          pathToApiSpec: path.join(
+            openApiSpecsDir,
+            'leastTemplatedPathAfterMostTemplatedPath',
+            `openapi${openApiVersion}.yml`,
+          ),
+        },
+      ];
+
+      openApiSpecs.forEach((spec) => {
+        const { pathToApiSpec, isLeastTemplatedPathFirst } = spec;
+
+        describe(`res.req.path matches a non-templated OpenAPI path ${
+          isLeastTemplatedPathFirst ? 'before' : 'after'
+        } a templated OpenAPI path`, () => {
+          const res = {
+            status: 200,
+            req: {
+              method: 'GET',
+              path:
+                '/preferLeastTemplatedPathOverMostTemplatedPath/templatedPath/nonTemplatedPath',
+            },
+            body: 'valid body (string)',
+          };
+
+          beforeAll(() => {
+            jestOpenAPI(pathToApiSpec);
+          });
+
+          it('passes', () => {
+            expect(res).toSatisfyApiSpec();
+          });
+
+          it('fails when using .not', () => {
+            const assertion = () => expect(res).not.toSatisfyApiSpec();
+            expect(assertion).toThrow(
+              "not to satisfy the '200' response defined for endpoint 'GET /preferLeastTemplatedPathOverMostTemplatedPath/{templatedPath}/nonTemplatedPath'",
+            );
+          });
+        });
+      });
+    });
+  });
+});
diff --git a/packages/openapi-validator/lib/utils/common.utils.ts b/packages/openapi-validator/lib/utils/common.utils.ts
index d789c7ec..2cc03ed7 100644
--- a/packages/openapi-validator/lib/utils/common.utils.ts
+++ b/packages/openapi-validator/lib/utils/common.utils.ts
@@ -21,20 +21,29 @@ const doesOpenApiPathMatchPathname = (openApiPath, pathname) => {
   return doesColonPathMatchPathname(pathInColonForm, pathname);
 };
 
+const countPathParams = (openApiPath) => {
+  return (openApiPath.match(/\{/g) || []).length;
+};
+
 export const findOpenApiPathMatchingPossiblePathnames = (
   possiblePathnames,
   OAPaths,
 ) => {
   let openApiPath;
+  let nbPathParams = -1;
   // eslint-disable-next-line no-restricted-syntax
   for (const pathname of possiblePathnames) {
     // eslint-disable-next-line no-restricted-syntax
     for (const OAPath of OAPaths) {
+      const count = countPathParams(OAPath);
       if (OAPath === pathname) {
         return OAPath;
       }
       if (doesOpenApiPathMatchPathname(OAPath, pathname)) {
-        openApiPath = OAPath;
+        if (nbPathParams == -1 || count < nbPathParams) {
+          nbPathParams = count;
+          openApiPath = OAPath;
+        }
       }
     }
   }