diff --git a/database/migrations/1693469174909-AddWaitingListIdToReservation.ts b/database/migrations/1693469174909-AddWaitingListIdToReservation.ts
new file mode 100644
index 0000000..b2c9882
--- /dev/null
+++ b/database/migrations/1693469174909-AddWaitingListIdToReservation.ts
@@ -0,0 +1,33 @@
+import { MigrationInterface, QueryRunner } from 'typeorm'
+
+export class AddWaitingListIdToReservation1693469174909
+	implements MigrationInterface
+{
+	name = 'AddWaitingListIdToReservation1693469174909'
+
+	public async up(queryRunner: QueryRunner): Promise<void> {
+		await queryRunner.query(
+			`CREATE TABLE "temporary_reservations" ("id" varchar PRIMARY KEY NOT NULL, "username" varchar(64) NOT NULL, "password" varchar(255) NOT NULL, "dateRangeStart" datetime NOT NULL, "dateRangeEnd" datetime NOT NULL, "opponentId" varchar(32) NOT NULL, "opponentName" varchar(255) NOT NULL, "waitListed" boolean NOT NULL DEFAULT (0), "waitingListId" integer)`,
+		)
+		await queryRunner.query(
+			`INSERT INTO "temporary_reservations"("id", "username", "password", "dateRangeStart", "dateRangeEnd", "opponentId", "opponentName", "waitListed") SELECT "id", "username", "password", "dateRangeStart", "dateRangeEnd", "opponentId", "opponentName", "waitListed" FROM "reservations"`,
+		)
+		await queryRunner.query(`DROP TABLE "reservations"`)
+		await queryRunner.query(
+			`ALTER TABLE "temporary_reservations" RENAME TO "reservations"`,
+		)
+	}
+
+	public async down(queryRunner: QueryRunner): Promise<void> {
+		await queryRunner.query(
+			`ALTER TABLE "reservations" RENAME TO "temporary_reservations"`,
+		)
+		await queryRunner.query(
+			`CREATE TABLE "reservations" ("id" varchar PRIMARY KEY NOT NULL, "username" varchar(64) NOT NULL, "password" varchar(255) NOT NULL, "dateRangeStart" datetime NOT NULL, "dateRangeEnd" datetime NOT NULL, "opponentId" varchar(32) NOT NULL, "opponentName" varchar(255) NOT NULL, "waitListed" boolean NOT NULL DEFAULT (0))`,
+		)
+		await queryRunner.query(
+			`INSERT INTO "reservations"("id", "username", "password", "dateRangeStart", "dateRangeEnd", "opponentId", "opponentName", "waitListed") SELECT "id", "username", "password", "dateRangeStart", "dateRangeEnd", "opponentId", "opponentName", "waitListed" FROM "temporary_reservations"`,
+		)
+		await queryRunner.query(`DROP TABLE "temporary_reservations"`)
+	}
+}
diff --git a/src/reservations/entity.ts b/src/reservations/entity.ts
index cfc2d1f..afc071c 100644
--- a/src/reservations/entity.ts
+++ b/src/reservations/entity.ts
@@ -68,6 +68,9 @@ export class Reservation {
 	@Column('boolean', { default: false })
 	waitListed: boolean
 
+	@Column('int', { nullable: true })
+	waitingListId: number
+
 	constructor(partial: Partial<Reservation>) {
 		Object.assign(this, partial)
 	}
diff --git a/src/reservations/service.ts b/src/reservations/service.ts
index 4e7b6f5..bbbf6aa 100644
--- a/src/reservations/service.ts
+++ b/src/reservations/service.ts
@@ -1,8 +1,9 @@
-import { Injectable } from '@nestjs/common'
+import { Inject, Injectable } from '@nestjs/common'
 import { InjectRepository } from '@nestjs/typeorm'
 import { Repository } from 'typeorm'
 
 import dayjs from '../common/dayjs'
+import { BaanReserverenService } from '../runner/baanreserveren/service'
 import { Reservation } from './entity'
 
 @Injectable()
@@ -10,6 +11,9 @@ export class ReservationsService {
 	constructor(
 		@InjectRepository(Reservation)
 		private reservationsRepository: Repository<Reservation>,
+
+		@Inject(BaanReserverenService)
+		private readonly brService: BaanReserverenService,
 	) {}
 
 	async getAll() {
@@ -45,6 +49,10 @@ export class ReservationsService {
 	}
 
 	async deleteById(id: string) {
-		return await this.reservationsRepository.delete({ id })
+		const reservation = await this.getById(id)
+		if (!reservation) return
+
+		await this.brService.removeReservationFromWaitList(reservation)
+		return await this.reservationsRepository.delete({ id: reservation.id })
 	}
 }
diff --git a/src/reservations/worker.ts b/src/reservations/worker.ts
index 3600743..f766b6e 100644
--- a/src/reservations/worker.ts
+++ b/src/reservations/worker.ts
@@ -66,9 +66,12 @@ export class ReservationsWorker {
 
 	async addReservationToWaitList(reservation: Reservation) {
 		try {
-			await this.brService.addReservationToWaitList(reservation)
+			const waitingListId = await this.brService.addReservationToWaitList(
+				reservation,
+			)
 			await this.reservationsService.update(reservation.id, {
 				waitListed: true,
+				waitingListId,
 			})
 		} catch (error: unknown) {
 			this.loggerService.error(
diff --git a/src/runner/baanreserveren/service.ts b/src/runner/baanreserveren/service.ts
index d1fc831..b8eac77 100644
--- a/src/runner/baanreserveren/service.ts
+++ b/src/runner/baanreserveren/service.ts
@@ -73,7 +73,7 @@ export class BaanReserverenService {
 	private startSession(username: string) {
 		this.loggerService.debug('Starting session', { username })
 		if (this.session && this.session.username !== username) {
-			throw new Error('Session already started')
+			throw new SessionStartError('Session already started')
 		}
 
 		if (this.session?.username === username) {
@@ -160,7 +160,7 @@ export class BaanReserverenService {
 		this.loggerService.debug('Navigating to day', { date })
 		if (this.getLastVisibleDay().isBefore(date)) {
 			await this.page
-				?.waitForSelector('td.month.next')
+				.waitForSelector('td.month.next')
 				.then((d) => d?.click())
 				.catch((e: Error) => {
 					this.loggerService.error('Failed to switch months', { error: e })
@@ -168,7 +168,7 @@ export class BaanReserverenService {
 				})
 		}
 		await this.page
-			?.waitForSelector(
+			.waitForSelector(
 				`td#cal_${date.get('year')}_${date.get('month') + 1}_${date.get(
 					'date',
 				)}`,
@@ -179,7 +179,7 @@ export class BaanReserverenService {
 				throw new RunnerNavigationDayError(e)
 			})
 		await this.page
-			?.waitForSelector(
+			.waitForSelector(
 				`td#cal_${date.get('year')}_${date.get('month') + 1}_${date.get(
 					'date',
 				)}.selected`,
@@ -210,6 +210,53 @@ export class BaanReserverenService {
 			})
 	}
 
+	private async recordWaitingListEntries(): Promise<number[]> {
+		const waitingListEntriesElements = await this.page.$$(
+			'#content tbody tr td:nth-child(1)',
+		)
+		if (!waitingListEntriesElements) return []
+
+		const waitingListIds = (
+			await Promise.all(
+				waitingListEntriesElements.map(async (e) => {
+					const elementTextContent = await (
+						await e.getProperty('textContent')
+					).jsonValue()
+
+					if (elementTextContent) {
+						return Number.parseInt(elementTextContent)
+					}
+				}),
+			)
+		).filter((id): id is number => id != null && typeof id === 'number')
+
+		return waitingListIds
+	}
+
+	private findNewWaitingListEntryId(
+		previous: number[],
+		current: number[],
+	): number | null {
+		const previousSet = new Set(previous)
+		for (const c of current) {
+			if (!previousSet.has(c)) return c
+		}
+
+		return null
+	}
+
+	private async deleteWaitingListEntryRowById(id: number) {
+		const rows = await this.page.$x(`//td[text()="${id}"]/parent::tr`)
+		if (rows.length === 0) {
+			throw new WaitingListEntryDeletionError(
+				'Cannot find waiting list entry to delete',
+			)
+		}
+
+		const deleteButton = await rows[0].$('a.wl-delete')
+		await deleteButton?.click()
+	}
+
 	private async openWaitingListDialog() {
 		this.loggerService.debug('Opening waiting list dialog')
 		await this.page.waitForNetworkIdle()
@@ -231,7 +278,7 @@ export class BaanReserverenService {
 			const timeString = possibleDate.format('HH:mm')
 			const selector =
 				`tr[data-time='${timeString}']` + `> td.free[rowspan='3'][type='free']`
-			freeCourt = await this.page?.$(selector)
+			freeCourt = await this.page.$(selector)
 			i++
 		}
 
@@ -249,7 +296,7 @@ export class BaanReserverenService {
 	private async selectOpponent(id: string, name: string) {
 		this.loggerService.debug('Selecting opponent', { id, name })
 		const player2Search = await this.page
-			?.waitForSelector('input:has(~ select[name="players[2]"])')
+			.waitForSelector('input:has(~ select[name="players[2]"])')
 			.catch((e: Error) => {
 				throw new RunnerOpponentSearchError(e)
 			})
@@ -258,11 +305,11 @@ export class BaanReserverenService {
 			.catch((e: Error) => {
 				throw new RunnerOpponentSearchInputError(e)
 			})
-		await this.page?.waitForNetworkIdle().catch((e: Error) => {
+		await this.page.waitForNetworkIdle().catch((e: Error) => {
 			throw new RunnerOpponentSearchNetworkError(e)
 		})
 		await this.page
-			?.$('select.br-user-select[name="players[2]"]')
+			.$('select.br-user-select[name="players[2]"]')
 			.then((d) => d?.select(id))
 			.catch((e: Error) => {
 				throw new RunnerOpponentSearchSelectionError(e)
@@ -272,13 +319,13 @@ export class BaanReserverenService {
 	private async confirmReservation() {
 		this.loggerService.debug('Confirming reservation')
 		await this.page
-			?.$('input#__make_submit')
+			.$('input#__make_submit')
 			.then((b) => b?.click())
 			.catch((e: Error) => {
 				throw new RunnerReservationConfirmButtonError(e)
 			})
 		await this.page
-			?.waitForSelector('input#__make_submit2')
+			.waitForSelector('input#__make_submit2')
 			.then((b) => b?.click())
 			.catch((e: Error) => {
 				throw new RunnerReservationConfirmSubmitError(e)
@@ -287,7 +334,7 @@ export class BaanReserverenService {
 
 	private async inputWaitingListDetails(reservation: Reservation) {
 		this.loggerService.debug('Inputting waiting list details')
-		const startDateInput = await this.page?.$('input[name="start_date"]')
+		const startDateInput = await this.page.$('input[name="start_date"]')
 		// Click 3 times to select all existing text
 		await startDateInput?.click({ count: 3, delay: 10 }).catch((e) => {
 			throw new RunnerWaitingListInputError(e)
@@ -300,7 +347,7 @@ export class BaanReserverenService {
 				throw new RunnerWaitingListInputError(e)
 			})
 
-		const endDateInput = await this.page?.$('input[name="end_date"]')
+		const endDateInput = await this.page.$('input[name="end_date"]')
 		await endDateInput
 			?.type(reservation.dateRangeEnd.format('DD-MM-YYYY'), {
 				delay: this.getTypingDelay(),
@@ -309,7 +356,7 @@ export class BaanReserverenService {
 				throw new RunnerWaitingListInputError(e)
 			})
 
-		const startTimeInput = await this.page?.$('input[name="start_time"]')
+		const startTimeInput = await this.page.$('input[name="start_time"]')
 		await startTimeInput
 			?.type(reservation.dateRangeStart.format('HH:mm'), {
 				delay: this.getTypingDelay(),
@@ -319,7 +366,7 @@ export class BaanReserverenService {
 			})
 
 		// Use the same time for start and end so that the waiting list only notifies for start time
-		const endTimeInput = await this.page?.$('input[name="end_time"]')
+		const endTimeInput = await this.page.$('input[name="end_time"]')
 		await endTimeInput
 			?.type(reservation.dateRangeStart.add(1, 'minutes').format('HH:mm'), {
 				delay: this.getTypingDelay(),
@@ -331,7 +378,7 @@ export class BaanReserverenService {
 
 	private async confirmWaitingListDetails() {
 		this.loggerService.debug('Confirming waiting list details')
-		const saveButton = await this.page?.$('input[type="submit"][value="Save"]')
+		const saveButton = await this.page.$('input[type="submit"][value="Save"]')
 		await saveButton?.click().catch((e) => {
 			throw new RunnerWaitingListConfirmError(e)
 		})
@@ -348,9 +395,31 @@ export class BaanReserverenService {
 	public async addReservationToWaitList(reservation: Reservation) {
 		await this.init(reservation)
 		await this.navigateToWaitingList()
+		const previousWaitingListIds = await this.recordWaitingListEntries()
 		await this.openWaitingListDialog()
 		await this.inputWaitingListDetails(reservation)
 		await this.confirmWaitingListDetails()
+		const currentWaitingListIds = await this.recordWaitingListEntries()
+		const waitingListId = this.findNewWaitingListEntryId(
+			previousWaitingListIds,
+			currentWaitingListIds,
+		)
+
+		if (waitingListId == null) {
+			throw new WaitingListSubmissionError(
+				'Failed to find new waiting list entry',
+			)
+		}
+
+		return waitingListId
+	}
+
+	public async removeReservationFromWaitList(reservation: Reservation) {
+		if (!reservation.waitListed || !reservation.waitingListId) return
+
+		await this.init(reservation)
+		await this.navigateToWaitingList()
+		await this.deleteWaitingListEntryRowById(reservation.waitingListId)
 	}
 }
 
@@ -498,3 +567,24 @@ export class RunnerReservationConfirmSubmitError extends RunnerError {
 		super(error, 'RunnerReservationConfirmSubmitError')
 	}
 }
+
+export class SessionStartError extends Error {
+	constructor(message: string) {
+		super(message)
+		this.name = 'SessionStartError'
+	}
+}
+
+export class WaitingListSubmissionError extends Error {
+	constructor(message: string) {
+		super(message)
+		this.name = 'WaitingListSubmissionError'
+	}
+}
+
+export class WaitingListEntryDeletionError extends Error {
+	constructor(message: string) {
+		super(message)
+		this.name = 'WaitingListEntryDeletionError'
+	}
+}