diff --git a/report-viewer/src/components/fileDisplaying/FilesContainer.vue b/report-viewer/src/components/fileDisplaying/FilesContainer.vue
index 7594bfb53..ede1c03ba 100644
--- a/report-viewer/src/components/fileDisplaying/FilesContainer.vue
+++ b/report-viewer/src/components/fileDisplaying/FilesContainer.vue
@@ -16,15 +16,13 @@
     </div>
 
     <ScrollableComponent class="flex-grow" ref="scrollContainer">
-      <VueDraggableNext>
+      <VueDraggableNext @update="emitFileMoving()">
         <CodePanel
-          v-for="(file, index) in files"
-          :key="index"
+          v-for="file in sortedFiles"
+          :key="file.fileName"
           ref="codePanels"
           :file="file"
-          :matches="
-            !matches.get(file.fileName) ? [] : (matches.get(file.fileName) as MatchInSingleFile[])
-          "
+          :matches="matchesPerFile[file.fileName]"
           :highlight-language="highlightLanguage"
           @match-selected="(match: Match) => $emit('matchSelected', match)"
           class="mt-1 first:mt-0"
@@ -48,6 +46,8 @@ import { FontAwesomeIcon } from '@fortawesome/vue-fontawesome'
 import { faCompressAlt } from '@fortawesome/free-solid-svg-icons'
 import { library } from '@fortawesome/fontawesome-svg-core'
 import type { Language } from '@/model/Language'
+import { FileSortingOptions } from '@/model/ui/FileSortingOptions'
+import { store } from '@/stores/store'
 import type { BaseCodeMatch } from '@/model/BaseCodeReport'
 import type { Match } from '@/model/Match'
 
@@ -91,7 +91,78 @@ const props = defineProps({
   }
 })
 
-defineEmits(['matchSelected'])
+const emit = defineEmits(['matchSelected', 'filesMoved'])
+
+const matchesPerFile = computed(() => {
+  const matches: Record<string, MatchInSingleFile[]> = {}
+  for (const file of props.files) {
+    matches[file.fileName] = !props.matches.get(file.fileName)
+      ? []
+      : (props.matches.get(file.fileName) as MatchInSingleFile[])
+  }
+  return matches
+})
+
+const sortedFiles: Ref<SubmissionFile[]> = ref([])
+sortFiles(store().uiState.fileSorting ?? FileSortingOptions.ALPHABETICAL)
+
+function sortFiles(fileSorting: FileSortingOptions) {
+  switch (fileSorting) {
+    case FileSortingOptions.ALPHABETICAL: {
+      sortedFiles.value = Array.from(props.files).sort((a, b) =>
+        a.fileName.localeCompare(b.fileName)
+      )
+      break
+    }
+
+    case FileSortingOptions.MATCH_SIZE: {
+      const largestMatch: Record<string, number> = {}
+      for (const file of props.files) {
+        largestMatch[file.fileName] = Math.max(
+          ...matchesPerFile.value[file.fileName].map((match) => match.match.tokens)
+        )
+      }
+      sortedFiles.value = Array.from(props.files).sort(
+        (a, b) => largestMatch[b.fileName] - largestMatch[a.fileName]
+      )
+      break
+    }
+
+    case FileSortingOptions.MATCH_COUNT: {
+      const matchCount: Record<string, number> = {}
+      for (const file of props.files) {
+        matchCount[file.fileName] = matchesPerFile.value[file.fileName].length
+      }
+      sortedFiles.value = Array.from(props.files).sort(
+        (a, b) => matchCount[b.fileName] - matchCount[a.fileName]
+      )
+      break
+    }
+
+    case FileSortingOptions.MATCH_COVERAGE: {
+      const matchCoverage: Record<string, number> = {}
+      for (const file of props.files) {
+        const matches = matchesPerFile.value[file.fileName]
+        const totalTokens = matches.reduce((acc, match) => acc + match.match.tokens, 0)
+        matchCoverage[file.fileName] =
+          totalTokens / (file.tokenCount > 0 ? file.tokenCount : Infinity)
+      }
+      sortedFiles.value = Array.from(props.files).sort(
+        (a, b) => matchCoverage[b.fileName] - matchCoverage[a.fileName]
+      )
+      break
+    }
+  }
+}
+
+const shouldEmitFileMoving = ref(true)
+
+function emitFileMoving() {
+  if (!shouldEmitFileMoving.value) {
+    return
+  }
+  emit('filesMoved')
+}
 
 const codePanels: Ref<(typeof CodePanel)[]> = ref([])
 const scrollContainer: Ref<typeof ScrollableComponent | null> = ref(null)
@@ -132,6 +203,7 @@ function collapseAll() {
 }
 
 defineExpose({
-  scrollTo
+  scrollTo,
+  sortFiles
 })
 </script>
diff --git a/report-viewer/src/components/optionsSelectors/OptionsSelectorComponent.vue b/report-viewer/src/components/optionsSelectors/OptionsSelectorComponent.vue
index 6be436228..b8abfd9f4 100644
--- a/report-viewer/src/components/optionsSelectors/OptionsSelectorComponent.vue
+++ b/report-viewer/src/components/optionsSelectors/OptionsSelectorComponent.vue
@@ -73,4 +73,8 @@ function select(index: number) {
   emit('selectionChanged', index)
   selected.value = index
 }
+
+defineExpose({
+  select
+})
 </script>
diff --git a/report-viewer/src/model/ui/FileSortingOptions.ts b/report-viewer/src/model/ui/FileSortingOptions.ts
new file mode 100644
index 000000000..8fe3d4837
--- /dev/null
+++ b/report-viewer/src/model/ui/FileSortingOptions.ts
@@ -0,0 +1,27 @@
+import type { ToolTipLabel } from './ToolTip'
+
+export enum FileSortingOptions {
+  ALPHABETICAL,
+  MATCH_COVERAGE,
+  MATCH_COUNT,
+  MATCH_SIZE
+}
+
+export const fileSortingTooltips: Record<FileSortingOptions, ToolTipLabel> = {
+  [FileSortingOptions.ALPHABETICAL]: {
+    displayValue: 'Alphabetical',
+    tooltip: 'Sort files alphabetically, similar to package structure.'
+  },
+  [FileSortingOptions.MATCH_COVERAGE]: {
+    displayValue: 'Match Coverage',
+    tooltip: 'Sort files by the percentage of tokens included in a match.'
+  },
+  [FileSortingOptions.MATCH_COUNT]: {
+    displayValue: 'Match Count',
+    tooltip: 'Sort files by the number of matches found.'
+  },
+  [FileSortingOptions.MATCH_SIZE]: {
+    displayValue: 'Match Size',
+    tooltip: 'Sort files by match size, with the largest matches at the top.'
+  }
+}
diff --git a/report-viewer/src/stores/state.ts b/report-viewer/src/stores/state.ts
index 8ef4a0521..b1f031c87 100644
--- a/report-viewer/src/stores/state.ts
+++ b/report-viewer/src/stores/state.ts
@@ -1,6 +1,7 @@
 import type { SubmissionFile } from '@/model/File'
 import type { MetricType } from '@/model/MetricType'
 import type { DistributionChartConfig } from '@/model/ui/DistributionChartConfig'
+import type { FileSortingOptions } from '@/model/ui/FileSortingOptions'
 
 /**
  * Local store. Stores the state of the application.
@@ -49,4 +50,5 @@ export interface UIState {
   comparisonTableSortingMetric: MetricType
   comparisonTableClusterSorting: boolean
   distributionChartConfig: DistributionChartConfig
+  fileSorting: FileSortingOptions
 }
diff --git a/report-viewer/src/stores/store.ts b/report-viewer/src/stores/store.ts
index e798cc207..5a721662e 100644
--- a/report-viewer/src/stores/store.ts
+++ b/report-viewer/src/stores/store.ts
@@ -2,6 +2,7 @@ import { defineStore } from 'pinia'
 import type { State, UIState } from './state'
 import { MetricType } from '@/model/MetricType'
 import type { SubmissionFile, File } from '@/model/File'
+import { FileSortingOptions } from '@/model/ui/FileSortingOptions'
 
 /**
  * The store is a global state management system. It is used to store the state of the application.
@@ -31,7 +32,8 @@ const store = defineStore('store', {
         metric: MetricType.AVERAGE,
         xScale: 'linear',
         bucketCount: 10
-      }
+      },
+      fileSorting: FileSortingOptions.ALPHABETICAL
     }
   }),
   getters: {
diff --git a/report-viewer/src/views/ComparisonView.vue b/report-viewer/src/views/ComparisonView.vue
index 996983cfa..e0a0860db 100644
--- a/report-viewer/src/views/ComparisonView.vue
+++ b/report-viewer/src/views/ComparisonView.vue
@@ -73,6 +73,14 @@
           :basecode-in-second="secondBaseCodeMatches"
           @match-selected="showMatch"
         />
+        <OptionsSelectorComponent
+          class="mt-2"
+          ref="sortingOptionSelector"
+          title="File Sorting:"
+          :labels="sortingOptions.map((o) => fileSortingTooltips[o])"
+          @selectionChanged="(index: number) => changeFileSorting(index)"
+          :default-selected="sortingOptions.indexOf(store().uiState.fileSorting)"
+        />
       </Container>
     </div>
     <div ref="styleholder"></div>
@@ -87,6 +95,7 @@
         :highlight-language="language"
         :base-code-matches="firstBaseCodeMatches"
         @match-selected="showMatchInSecond"
+        @files-moved="filesMoved()"
         class="max-h-0 min-h-full flex-1 overflow-hidden print:max-h-none print:overflow-y-visible"
       />
       <FilesContainer
@@ -97,6 +106,7 @@
         :highlight-language="language"
         :base-code-matches="secondBaseCodeMatches"
         @match-selected="showMatchInFirst"
+        @files-moved="filesMoved()"
         class="max-h-0 min-h-full flex-1 overflow-hidden print:max-h-none print:overflow-y-visible"
       />
     </div>
@@ -122,6 +132,8 @@ import { MetricType } from '@/model/MetricType'
 import { Comparison } from '@/model/Comparison'
 import { redirectOnError } from '@/router'
 import ToolTipComponent from '@/components/ToolTipComponent.vue'
+import { FileSortingOptions, fileSortingTooltips } from '@/model/ui/FileSortingOptions'
+import OptionsSelectorComponent from '@/components/optionsSelectors/OptionsSelectorComponent.vue'
 import type { BaseCodeMatch } from '@/model/BaseCodeReport'
 
 library.add(faPrint)
@@ -178,6 +190,32 @@ function showMatch(match: Match) {
   showMatchInSecond(match)
 }
 
+const sortingOptions = [
+  FileSortingOptions.ALPHABETICAL,
+  FileSortingOptions.MATCH_COVERAGE,
+  FileSortingOptions.MATCH_COUNT,
+  FileSortingOptions.MATCH_SIZE
+]
+const movedAfterSorting = ref(false)
+const sortingOptionSelector: Ref<typeof OptionsSelectorComponent | null> = ref(null)
+
+function changeFileSorting(index: number) {
+  movedAfterSorting.value = false
+  if (index < 0) {
+    return
+  }
+  store().uiState.fileSorting = sortingOptions[index]
+  panel1.value?.sortFiles(store().uiState.fileSorting)
+  panel2.value?.sortFiles(store().uiState.fileSorting)
+}
+
+function filesMoved() {
+  movedAfterSorting.value = true
+  if (sortingOptionSelector.value) {
+    sortingOptionSelector.value.select(-2)
+  }
+}
+
 function print() {
   window.print()
 }