diff --git a/packages/@aws-cdk/assertions/README.md b/packages/@aws-cdk/assertions/README.md
index d2763d0ba24ef..0c2d9d1ecdadf 100644
--- a/packages/@aws-cdk/assertions/README.md
+++ b/packages/@aws-cdk/assertions/README.md
@@ -129,9 +129,17 @@ assert.hasOutput('*', {
 });
 ```
 
-`findOutputs()` will return a list of outputs that match the `logicalId` and `props`,
+`findOutputs()` will return a set of outputs that match the `logicalId` and `props`,
 and you can use the `'*'` special case as well.
 
+```ts
+const result = assert.findOutputs('*', {
+  Value: 'Fred',
+});
+expect(result.Foo).toEqual({ Value: 'Fred', Description: 'FooFred' });
+expect(result.Bar).toEqual({ Value: 'Fred', Description: 'BarFred' });
+```
+
 The APIs `hasMapping()` and `findMappings()` provide similar functionalities.
 
 ## Special Matchers
diff --git a/packages/@aws-cdk/assertions/lib/private/mappings.ts b/packages/@aws-cdk/assertions/lib/private/mappings.ts
index 266e322bb1139..e19afe541d204 100644
--- a/packages/@aws-cdk/assertions/lib/private/mappings.ts
+++ b/packages/@aws-cdk/assertions/lib/private/mappings.ts
@@ -1,12 +1,12 @@
 import { StackInspector } from '../vendored/assert';
 import { filterLogicalId, formatFailure, matchSection } from './section';
 
-export function findMappings(inspector: StackInspector, logicalId: string, props: any = {}): { [key: string]: any }[] {
+export function findMappings(inspector: StackInspector, logicalId: string, props: any = {}): { [key: string]: { [key: string]: any } } {
   const section: { [key: string] : {} } = inspector.value.Mappings;
   const result = matchSection(filterLogicalId(section, logicalId), props);
 
   if (!result.match) {
-    return [];
+    return {};
   }
 
   return result.matches;
diff --git a/packages/@aws-cdk/assertions/lib/private/outputs.ts b/packages/@aws-cdk/assertions/lib/private/outputs.ts
index 870e00555b254..320016d22a8eb 100644
--- a/packages/@aws-cdk/assertions/lib/private/outputs.ts
+++ b/packages/@aws-cdk/assertions/lib/private/outputs.ts
@@ -1,12 +1,12 @@
 import { StackInspector } from '../vendored/assert';
 import { filterLogicalId, formatFailure, matchSection } from './section';
 
-export function findOutputs(inspector: StackInspector, logicalId: string, props: any = {}): { [key: string]: any }[] {
+export function findOutputs(inspector: StackInspector, logicalId: string, props: any = {}): { [key: string]: { [key: string]: any } } {
   const section: { [key: string] : {} } = inspector.value.Outputs;
   const result = matchSection(filterLogicalId(section, logicalId), props);
 
   if (!result.match) {
-    return [];
+    return {};
   }
 
   return result.matches;
diff --git a/packages/@aws-cdk/assertions/lib/private/resources.ts b/packages/@aws-cdk/assertions/lib/private/resources.ts
index 31286a8a6f1a4..81b77346f61f5 100644
--- a/packages/@aws-cdk/assertions/lib/private/resources.ts
+++ b/packages/@aws-cdk/assertions/lib/private/resources.ts
@@ -6,12 +6,12 @@ type Resource = {
   Type: string;
 }
 
-export function findResources(inspector: StackInspector, type: string, props: any = {}): { [key: string]: any }[] {
+export function findResources(inspector: StackInspector, type: string, props: any = {}): { [key: string]: { [key: string]: any } } {
   const section: { [key: string] : Resource } = inspector.value.Resources;
   const result = matchSection(filterType(section, type), props);
 
   if (!result.match) {
-    return [];
+    return {};
   }
 
   return result.matches;
diff --git a/packages/@aws-cdk/assertions/lib/private/section.ts b/packages/@aws-cdk/assertions/lib/private/section.ts
index 59ad55241e581..89242bc3d6005 100644
--- a/packages/@aws-cdk/assertions/lib/private/section.ts
+++ b/packages/@aws-cdk/assertions/lib/private/section.ts
@@ -1,22 +1,22 @@
 import { Match } from '../match';
 import { Matcher, MatchResult } from '../matcher';
 
-export type MatchSuccess = { match: true, matches: any[] };
+export type MatchSuccess = { match: true, matches: {[key: string]: any} };
 export type MatchFailure = { match: false, closestResult?: MatchResult, analyzedCount: number };
 
 export function matchSection(section: any, props: any): MatchSuccess | MatchFailure {
   const matcher = Matcher.isMatcher(props) ? props : Match.objectLike(props);
   let closestResult: MatchResult | undefined = undefined;
-  let matching: any[] = [];
+  let matching: {[key: string]: any} = {};
   let count = 0;
 
   eachEntryInSection(
     section,
 
-    (entry) => {
+    (logicalId, entry) => {
       const result = matcher.test(entry);
       if (!result.hasFailed()) {
-        matching.push(entry);
+        matching[logicalId] = entry;
       } else {
         count++;
         if (closestResult === undefined || closestResult.failCount > result.failCount) {
@@ -25,8 +25,7 @@ export function matchSection(section: any, props: any): MatchSuccess | MatchFail
       }
     },
   );
-
-  if (matching.length > 0) {
+  if (Object.keys(matching).length > 0) {
     return { match: true, matches: matching };
   } else {
     return { match: false, closestResult, analyzedCount: count };
@@ -35,11 +34,11 @@ export function matchSection(section: any, props: any): MatchSuccess | MatchFail
 
 function eachEntryInSection(
   section: any,
-  cb: (entry: {[key: string]: any}) => void): void {
+  cb: (logicalId: string, entry: {[key: string]: any}) => void): void {
 
   for (const logicalId of Object.keys(section ?? {})) {
     const resource: { [key: string]: any } = section[logicalId];
-    cb(resource);
+    cb(logicalId, resource);
   }
 }
 
diff --git a/packages/@aws-cdk/assertions/lib/template.ts b/packages/@aws-cdk/assertions/lib/template.ts
index d642e74962080..e6f721d928576 100644
--- a/packages/@aws-cdk/assertions/lib/template.ts
+++ b/packages/@aws-cdk/assertions/lib/template.ts
@@ -101,7 +101,7 @@ export class Template {
    * When a literal is provided, performs a partial match via `Match.objectLike()`.
    * Use the `Match` APIs to configure a different behaviour.
    */
-  public findResources(type: string, props: any = {}): { [key: string]: any }[] {
+  public findResources(type: string, props: any = {}): { [key: string]: { [key: string]: any } } {
     return findResources(this.inspector, type, props);
   }
 
@@ -126,7 +126,7 @@ export class Template {
    * When a literal object is provided, performs a partial match via `Match.objectLike()`.
    * Use the `Match` APIs to configure a different behaviour.
    */
-  public findOutputs(logicalId: string, props: any = {}): { [key: string]: any }[] {
+  public findOutputs(logicalId: string, props: any = {}): { [key: string]: { [key: string]: any } } {
     return findOutputs(this.inspector, logicalId, props);
   }
 
@@ -151,7 +151,7 @@ export class Template {
    * When a literal object is provided, performs a partial match via `Match.objectLike()`.
    * Use the `Match` APIs to configure a different behaviour.
    */
-  public findMappings(logicalId: string, props: any = {}): { [key: string]: any }[] {
+  public findMappings(logicalId: string, props: any = {}): { [key: string]: { [key: string]: any } } {
     return findMappings(this.inspector, logicalId, props);
   }
 
diff --git a/packages/@aws-cdk/assertions/test/private/section.test.ts b/packages/@aws-cdk/assertions/test/private/section.test.ts
index 20cc2d5d14e0b..28cdece823df7 100644
--- a/packages/@aws-cdk/assertions/test/private/section.test.ts
+++ b/packages/@aws-cdk/assertions/test/private/section.test.ts
@@ -18,7 +18,9 @@ describe('section', () => {
       // THEN
       expect(result.match).toEqual(true);
       const success = result as MatchSuccess;
-      expect(success.matches.length).toEqual(2);
+      expect(Object.keys(success.matches).length).toEqual(2);
+      expect(success.matches.Entry1).toEqual({ foo: 'bar' });
+      expect(success.matches.Entry2).toEqual({ foo: 'bar', baz: 'qux' });
     });
 
     test('failure', () => {
diff --git a/packages/@aws-cdk/assertions/test/template.test.ts b/packages/@aws-cdk/assertions/test/template.test.ts
index ca5c5c5ea1e58..7c3221763446c 100644
--- a/packages/@aws-cdk/assertions/test/template.test.ts
+++ b/packages/@aws-cdk/assertions/test/template.test.ts
@@ -278,10 +278,12 @@ describe('Template', () => {
       });
 
       const inspect = Template.fromStack(stack);
-      expect(inspect.findResources('Foo::Bar')).toEqual([{
-        Type: 'Foo::Bar',
-        Properties: { baz: 'qux', fred: 'waldo' },
-      }]);
+      expect(inspect.findResources('Foo::Bar')).toEqual({
+        Foo: {
+          Type: 'Foo::Bar',
+          Properties: { baz: 'qux', fred: 'waldo' },
+        },
+      });
     });
 
     test('no matching resource type', () => {
@@ -292,7 +294,7 @@ describe('Template', () => {
       });
 
       const inspect = Template.fromStack(stack);
-      expect(inspect.findResources('Foo::Baz')).toEqual([]);
+      expect(inspect.findResources('Foo::Baz')).toEqual({});
     });
 
     test('matching resource props', () => {
@@ -303,9 +305,9 @@ describe('Template', () => {
       });
 
       const inspect = Template.fromStack(stack);
-      expect(inspect.findResources('Foo::Bar', {
+      expect(Object.keys(inspect.findResources('Foo::Bar', {
         Properties: { baz: 'qux' },
-      }).length).toEqual(1);
+      })).length).toEqual(1);
     });
 
     test('no matching resource props', () => {
@@ -318,7 +320,7 @@ describe('Template', () => {
       const inspect = Template.fromStack(stack);
       expect(inspect.findResources('Foo::Bar', {
         Properties: { baz: 'waldo' },
-      })).toEqual([]);
+      })).toEqual({});
     });
 
     test('multiple matching resources', () => {
@@ -327,7 +329,10 @@ describe('Template', () => {
       new CfnResource(stack, 'Bar', { type: 'Foo::Bar' });
 
       const inspect = Template.fromStack(stack);
-      expect(inspect.findResources('Foo::Bar').length).toEqual(2);
+      const result = inspect.findResources('Foo::Bar');
+      expect(Object.keys(result).length).toEqual(2);
+      expect(result.Foo).toEqual({ Type: 'Foo::Bar' });
+      expect(result.Bar).toEqual({ Type: 'Foo::Bar' });
     });
   });
 
@@ -433,10 +438,9 @@ describe('Template', () => {
 
       const inspect = Template.fromStack(stack);
       const result = inspect.findOutputs('*', { Value: 'Fred' });
-      expect(result).toEqual([
-        { Value: 'Fred', Description: 'FooFred' },
-        { Value: 'Fred', Description: 'BarFred' },
-      ]);
+      expect(Object.keys(result).length).toEqual(2);
+      expect(result.Foo).toEqual({ Value: 'Fred', Description: 'FooFred' });
+      expect(result.Bar).toEqual({ Value: 'Fred', Description: 'BarFred' });
     });
 
     test('not matching', () => {
@@ -447,7 +451,7 @@ describe('Template', () => {
 
       const inspect = Template.fromStack(stack);
       const result = inspect.findOutputs('*', { Value: 'Waldo' });
-      expect(result.length).toEqual(0);
+      expect(Object.keys(result).length).toEqual(0);
     });
 
     test('matching specific output', () => {
@@ -461,9 +465,11 @@ describe('Template', () => {
 
       const inspect = Template.fromStack(stack);
       const result = inspect.findOutputs('Foo', { Value: 'Fred' });
-      expect(result).toEqual([
-        { Value: 'Fred' },
-      ]);
+      expect(result).toEqual({
+        Foo: {
+          Value: 'Fred',
+        },
+      });
     });
 
     test('not matching specific output', () => {
@@ -477,7 +483,7 @@ describe('Template', () => {
 
       const inspect = Template.fromStack(stack);
       const result = inspect.findOutputs('Foo', { Value: 'Waldo' });
-      expect(result.length).toEqual(0);
+      expect(Object.keys(result).length).toEqual(0);
     });
   });
 
@@ -592,13 +598,13 @@ describe('Template', () => {
 
       const inspect = Template.fromStack(stack);
       const result = inspect.findMappings('*', { Foo: { Bar: 'Lightning' } });
-      expect(result).toEqual([
-        {
+      expect(result).toEqual({
+        Foo: {
           Foo: { Bar: 'Lightning', Fred: 'Waldo' },
           Baz: { Bar: 'Qux' },
         },
-        { Foo: { Bar: 'Lightning' } },
-      ]);
+        Fred: { Foo: { Bar: 'Lightning' } },
+      });
     });
 
     test('not matching', () => {
@@ -611,7 +617,7 @@ describe('Template', () => {
 
       const inspect = Template.fromStack(stack);
       const result = inspect.findMappings('*', { Foo: { Bar: 'Waldo' } });
-      expect(result.length).toEqual(0);
+      expect(Object.keys(result).length).toEqual(0);
     });
 
     test('matching with specific outputName', () => {
@@ -630,15 +636,15 @@ describe('Template', () => {
 
       const inspect = Template.fromStack(stack);
       const result = inspect.findMappings('Foo', { Foo: { Bar: 'Lightning' } });
-      expect(result).toEqual([
-        {
+      expect(result).toEqual({
+        Foo: {
           Foo: { Bar: 'Lightning', Fred: 'Waldo' },
           Baz: { Bar: 'Qux' },
         },
-      ]);
+      });
     });
 
-    test('not matching', () => {
+    test('not matching specific output name', () => {
       const stack = new Stack();
       new CfnMapping(stack, 'Foo', {
         mapping: {
@@ -654,7 +660,7 @@ describe('Template', () => {
 
       const inspect = Template.fromStack(stack);
       const result = inspect.findMappings('Fred', { Baz: { Bar: 'Qux' } });
-      expect(result.length).toEqual(0);
+      expect(Object.keys(result).length).toEqual(0);
     });
   });
 });
diff --git a/packages/@aws-cdk/aws-apigatewayv2/test/http/api.test.ts b/packages/@aws-cdk/aws-apigatewayv2/test/http/api.test.ts
index a4e880bac742d..dc096594d0ecd 100644
--- a/packages/@aws-cdk/aws-apigatewayv2/test/http/api.test.ts
+++ b/packages/@aws-cdk/aws-apigatewayv2/test/http/api.test.ts
@@ -267,9 +267,9 @@ describe('HttpApi', () => {
     Template.fromStack(stack).hasResourceProperties('AWS::ApiGatewayV2::VpcLink', {
       Name: 'Link-1',
     });
-    expect(Template.fromStack(stack).findResources('AWS::ApiGatewayV2::VpcLink', {
+    expect(Object.keys(Template.fromStack(stack).findResources('AWS::ApiGatewayV2::VpcLink', {
       Name: 'Link-2',
-    }).length).toEqual(0);
+    })).length).toEqual(0);
   });
 
   test('apiEndpoint is exported', () => {
diff --git a/packages/@aws-cdk/aws-cloudwatch/test/dashboard.test.ts b/packages/@aws-cdk/aws-cloudwatch/test/dashboard.test.ts
index 6e796aa6b833b..201f0158c11c3 100644
--- a/packages/@aws-cdk/aws-cloudwatch/test/dashboard.test.ts
+++ b/packages/@aws-cdk/aws-cloudwatch/test/dashboard.test.ts
@@ -27,8 +27,9 @@ describe('Dashboard', () => {
 
     // THEN
     const resources = Template.fromStack(stack).findResources('AWS::CloudWatch::Dashboard');
-    expect(resources.length).toEqual(1);
-    hasWidgets(resources[0].Properties, [
+    expect(Object.keys(resources).length).toEqual(1);
+    const key = Object.keys(resources)[0];
+    hasWidgets(resources[key].Properties, [
       { type: 'text', width: 10, height: 2, x: 0, y: 0, properties: { markdown: 'first' } },
       { type: 'text', width: 1, height: 4, x: 0, y: 2, properties: { markdown: 'second' } },
       { type: 'text', width: 4, height: 1, x: 0, y: 6, properties: { markdown: 'third' } },
@@ -63,8 +64,9 @@ describe('Dashboard', () => {
 
     // THEN
     const resources = Template.fromStack(stack).findResources('AWS::CloudWatch::Dashboard');
-    expect(resources.length).toEqual(1);
-    hasWidgets(resources[0].Properties, [
+    expect(Object.keys(resources).length).toEqual(1);
+    const key = Object.keys(resources)[0];
+    hasWidgets(resources[key].Properties, [
       { type: 'text', width: 10, height: 2, x: 0, y: 0, properties: { markdown: 'first' } },
       { type: 'text', width: 1, height: 4, x: 10, y: 0, properties: { markdown: 'second' } },
       { type: 'text', width: 4, height: 1, x: 11, y: 0, properties: { markdown: 'third' } },