diff --git a/packages/frontend/src/components/MkDrive.vue b/packages/frontend/src/components/MkDrive.vue
index 03b1f17c78..81f25f115f 100644
--- a/packages/frontend/src/components/MkDrive.vue
+++ b/packages/frontend/src/components/MkDrive.vue
@@ -69,25 +69,28 @@ SPDX-License-Identifier: AGPL-3.0-only
 				<MkButton v-if="foldersPaginator.canFetchOlder" ref="moreFolders" @click="foldersPaginator.fetchOlder()">{{ i18n.ts.loadMore }}</MkButton>
 			</div>
 
-			<div v-show="filesPaginator.items.value.length > 0" ref="filesContainer" :class="$style.files">
-				<div v-for="(file, i) in filesPaginator.items.value" :key="file.id">
-					<div v-if="i > 0 && isSeparatorNeeded(filesPaginator.items.value[i -1].createdAt, file.createdAt)" :class="$style.date">
-						<span><i class="ti ti-chevron-up"></i> {{ getSeparatorInfo(filesPaginator.items.value[i -1].createdAt, file.createdAt).prevText }}</span>
-						<span style="height: 1em; width: 1px; background: var(--MI_THEME-divider);"></span>
-						<span>{{ getSeparatorInfo(filesPaginator.items.value[i -1].createdAt, file.createdAt).nextText }} <i class="ti ti-chevron-down"></i></span>
+			<div v-show="filesPaginator.items.value.length > 0" ref="filesContainer">
+				<MkStickyContainer v-for="(item, i) in filesTimeline" :key="item.date.toISOString()">
+					<template #header>
+						<div :class="$style.date">
+							<span><i class="ti ti-chevron-down"></i> {{ item.date.getFullYear() }}/{{ item.date.getMonth() + 1 }}/{{ item.date.getDate() }}</span>
+						</div>
+					</template>
+
+					<div :class="$style.files">
+						<XFile
+							v-for="file in item.items" :key="file.id"
+							:class="$style.file"
+							:file="file"
+							:folder="folder"
+							:selectMode="select === 'file'"
+							:isSelected="selectedFiles.some(x => x.id === file.id)"
+							@chosen="chooseFile"
+							@dragstart="isDragSource = true"
+							@dragend="isDragSource = false"
+						/>
 					</div>
-					<XFile
-						v-else
-						:class="$style.file"
-						:file="file"
-						:folder="folder"
-						:selectMode="select === 'file'"
-						:isSelected="selectedFiles.some(x => x.id === file.id)"
-						@chosen="chooseFile"
-						@dragstart="isDragSource = true"
-						@dragend="isDragSource = false"
-					/>
-				</div>
+				</MkStickyContainer>
 				<MkButton v-show="filesPaginator.canFetchOlder" ref="loadMoreFiles" @click="filesPaginator.fetchOlder()">{{ i18n.ts.loadMore }}</MkButton>
 			</div>
 
@@ -121,7 +124,7 @@ import { claimAchievement } from '@/utility/achievements.js';
 import { prefer } from '@/preferences.js';
 import { chooseFileFromPc } from '@/utility/select-file.js';
 import { store } from '@/store.js';
-import { isSeparatorNeeded, getSeparatorInfo } from '@/utility/timeline-date-separate.js';
+import { isSeparatorNeeded, getSeparatorInfo, makeDateGroupedTimelineComputedRef } from '@/utility/timeline-date-separate.js';
 import { usePagination } from '@/composables/use-pagination.js';
 
 const props = withDefaults(defineProps<{
@@ -183,6 +186,8 @@ const foldersPaginator = usePagination({
 	autoInit: false,
 });
 
+const filesTimeline = makeDateGroupedTimelineComputedRef(filesPaginator.items, 'month');
+
 watch(folder, () => emit('cd', folder.value));
 watch(sortModeSelect, () => {
 	initialize();
@@ -725,22 +730,9 @@ onBeforeUnmount(() => {
 
 .folders,
 .files {
-	display: flex;
-	flex-wrap: wrap;
-}
-
-.folder,
-.file {
-	flex-grow: 1;
-	width: 128px;
-	margin: 4px;
-	box-sizing: border-box;
-}
-
-.padding {
-	flex-grow: 1;
-	pointer-events: none;
-	width: 128px + 8px;
+	display: grid;
+	grid-template-columns: repeat(auto-fill, minmax(140px, 1fr));
+	grid-gap: 12px;
 }
 
 .empty {
diff --git a/packages/frontend/src/utility/timeline-date-separate.ts b/packages/frontend/src/utility/timeline-date-separate.ts
index 1071a80962..33ddea048b 100644
--- a/packages/frontend/src/utility/timeline-date-separate.ts
+++ b/packages/frontend/src/utility/timeline-date-separate.ts
@@ -4,7 +4,7 @@
  */
 
 import { computed } from 'vue';
-import type { Ref } from 'vue';
+import type { Ref, ShallowRef } from 'vue';
 
 export function getDateText(dateInstance: Date) {
 	const date = dateInstance.getDate();
@@ -12,19 +12,6 @@ export function getDateText(dateInstance: Date) {
 	return `${month.toString()}/${date.toString()}`;
 }
 
-export type DateSeparetedTimelineItem<T> = {
-	id: string;
-	type: 'item';
-	data: T;
-} | {
-	id: string;
-	type: 'date';
-	prev: Date;
-	prevText: string;
-	next: Date;
-	nextText: string;
-};
-
 // TODO: いちいちDateインスタンス作成するのは無駄感あるから文字列のまま解析したい
 export function isSeparatorNeeded(
 	prev: string | null,
@@ -56,7 +43,20 @@ export function getSeparatorInfo(
 	};
 }
 
-export function makeDateSeparatedTimelineComputedRef<T extends { id: string; createdAt: string; }>(items: Ref<T[]>) {
+export type DateSeparetedTimelineItem<T> = {
+	id: string;
+	type: 'item';
+	data: T;
+} | {
+	id: string;
+	type: 'date';
+	prev: Date;
+	prevText: string;
+	next: Date;
+	nextText: string;
+};
+
+export function makeDateSeparatedTimelineComputedRef<T extends { id: string; createdAt: string; }>(items: Ref<T[]> | ShallowRef<T[]>) {
 	return computed<DateSeparetedTimelineItem<T>[]>(() => {
 		const tl: DateSeparetedTimelineItem<T>[] = [];
 		for (let i = 0; i < items.value.length; i++) {
@@ -92,3 +92,35 @@ export function makeDateSeparatedTimelineComputedRef<T extends { id: string; cre
 		return tl;
 	});
 }
+
+export type DateGroupedTimelineItem<T> = {
+	date: Date;
+	items: T[];
+};
+
+export function makeDateGroupedTimelineComputedRef<T extends { id: string; createdAt: string; }>(items: Ref<T[]> | ShallowRef<T[]>, span: 'day' | 'month' = 'day') {
+	return computed<DateGroupedTimelineItem<T>[]>(() => {
+		const tl: DateGroupedTimelineItem<T>[] = [];
+		for (let i = 0; i < items.value.length; i++) {
+			const item = items.value[i];
+			const date = new Date(item.createdAt);
+			const nextDate = items.value[i + 1] ? new Date(items.value[i + 1].createdAt) : null;
+
+			if (tl.length === 0 || (
+				span === 'day' && tl[tl.length - 1].date.getTime() !== date.getTime()
+			) || (
+				span === 'month' && (
+					tl[tl.length - 1].date.getFullYear() !== date.getFullYear() ||
+					tl[tl.length - 1].date.getMonth() !== date.getMonth()
+				)
+			)) {
+				tl.push({
+					date,
+					items: [],
+				});
+			}
+			tl[tl.length - 1].items.push(item);
+		}
+		return tl;
+	});
+}