Wednesday marks five years since the UK voted to leave the EU by 52% to 48% – however, the path out of Europe has been anything but smooth.

Here are the key dates on Britain’s road to Brexit.

– January 23 2013

Under intense pressure from many of his own MPs and with the rise of Ukip, prime minister David Cameron promises an in-out referendum on EU membership if the Conservatives win the 2015 general election.

– May 7 2015

The Tories unexpectedly make sweeping gains over Ed Miliband’s Labour Party and secure a majority in the Commons. Mr Cameron vows to deliver his manifesto pledge of an EU referendum.

– June 23 2016

The UK votes to leave the EU in a shock result that sees 52% of the public support Brexit and Mr Cameron quickly resigns as prime minister.

EU referendum
The Brexit vote spells the end of David Cameron’s time as PM (Daniel Leal-Olivas/PA)

– July 13 2016

Theresa May takes over as prime minister. Despite having backed Remain, she promises to “rise to the challenge” of negotiating the UK’s exit.

– November 10 2016

The High Court rules against the Government and says Parliament must hold a vote to trigger Article 50 of the Treaty on European Union, the mechanism that begins the exit from the EU. Mrs May says the ruling will not stop her from invoking the legislation by April 2017.

– March 29 2017

Mrs May triggers Article 50. European Council president Donald Tusk says it is not a happy occasion, telling a Brussels press conference his message to the UK is: “We already miss you. Thank you and goodbye.”

– April 18 2017

Mrs May announces a snap general election to be held on June 8.

General Election 2017 aftermath
A disastrous election forces Theresa May into bed with the DUP (Dominic Lipinski/PA)

– June 8 2017

There is humiliation for Mrs May as she loses her Commons majority after her election gamble backfires. She becomes head of a minority Conservative administration propped up by the Democratic Unionist Party.

– September 22 2017

In a crucial Brexit speech in Florence, Mrs May sends a message to EU leaders by saying: “We want to be your strongest friend and partner as the EU and UK thrive side by side.” She says she is proposing an “implementation period” of “around two years” after Brexit when existing market access arrangements will apply.

– March 19 2018

The EU’s chief negotiator Michel Barnier says he and Brexit secretary David Davis have taken a “decisive step” towards agreeing a joint legal text on the UK’s EU withdrawal but warns there are still outstanding issues relating to the Irish border.

Brexit
Michel Barnier warns the Northern Irish border will be a major obstacle to Brexit (Liam McBurney/PA)

– July 6 2018

A crunch Cabinet meeting at Chequers agrees Mrs May’s new Brexit plans, including the creation of a new UK-EU free trade area for goods. But not all who attend are happy with the compromises.

– July 8 and July 9 2018

Mr Davis resigns from the Government in protest while the following day Boris Johnson quits as foreign secretary, claiming the plans mean “we are truly headed for the status of colony” of the EU.

– November 14 2018
In a statement outside 10 Downing Street after a five-hour Cabinet meeting, Mrs May says the Cabinet has agreed the draft Brexit Withdrawal Agreement.

Boris Johnson moving
Removal men outside the Foreign Secretary’s official residence after Boris Johnson’s resignation (Jonathan Brady/PA)

– November 15 2018

Dominic Raab resigns as Brexit secretary, saying he “cannot in good conscience support the terms proposed for our deal with the EU”. Other resignations follow.

– November 25 2018

The 27 EU leaders endorse the Brexit deal.

– December 12 2018

Mrs May survives an attempt to oust her with a vote of no confidence as Tory MPs vote by 200 to 117 in the secret ballot in Westminster.

– January 15 2019

MPs reject Mrs May’s Brexit plans by an emphatic 432 to 202 in an historic vote which throws the future of her administration and the nature of the UK’s EU withdrawal into doubt.

Brexit
Theresa May speaking in the House of Commons after her Brexit deal was rejected (House of Commons/PA)

– March 20 2019

Mrs May tells the House of Commons that she has written to Mr Tusk to request an extension to Article 50 Brexit negotiations to June 30.

– March 29 2019

MPs reject Mrs May’s Withdrawal Agreement for a third time – by 286 votes to 344 – on the day the UK was due to leave the EU.

– April 10 2019

The EU agrees a “flexible extension” to Brexit until October 31. Mrs May says the “choices we now face are stark and the timetable is clear”.

Brexit
Theresa May is forced to ask for a Brexit extension from Donald Tusk (ec.europa.eu/PA)

– May 23 2019

Nigel Farage’s Brexit Party comes out on top in the European elections, while the pro-EU Liberal Democrats also make gains.

– May 24 2019

Mrs May announces she is standing down as Tory Party leader on June 7. She says: “It is and will always remain a matter of deep regret to me that I have not been able to deliver Brexit.”

– July 23 2019

Mr Johnson is elected as leader of the Conservative Party and becomes the UK’s new Prime Minister after defeating Jeremy Hunt.

Tory leadership race
Boris Johnson becomes Conservative leader (Stefan Rousseau/PA)

– August 20 2019

The new Prime Minister is rebuffed by European Commission president Jean-Claude Juncker after demanding major changes to Irish border arrangements in a new Brexit deal.

– August 28 2019

The Queen is dragged into the Brexit row as Mr Johnson requests the prorogation of Parliament from early September to mid-October.

– September 4 2019

MPs vote to approve legislation aimed at preventing a no-deal Brexit. Mr Johnson orders a purge of rebel Tories who opposed the Government including former chancellors Philip Hammond and Sir Kenneth Clarke.

The Prime Minister attempts to trigger an early general election but fails to get the required support of two-thirds of MPs.

– September 24 2019

The Supreme Court rules that the PM’s advice to the Queen to suspend Parliament until October 14 was unlawful because it had the effect of frustrating Parliament.

Brexit
Lady Hale’s spider broach became a Remainer symbol after the Supreme Court’s Parliament ruling (Supreme Court/ PA)

– October 2 2019

Mr Johnson puts forward his formal Brexit plan to the EU, revealing his blueprint to solve the Irish border issue.

– October 10 2019

Mr Johnson and taoiseach Leo Varadkar say they can see a “pathway to a deal”, in a joint statement after key talks at a luxury hotel in Cheshire.

– October 17 2019

After intense negotiations, the Prime Minister announces the UK has reached a “great deal” with the EU which “takes back control” and means that “the UK can come out of the EU as one United Kingdom – England, Scotland, Wales, Northern Ireland, together”.

– October 19 2019

In the first Saturday sitting of the Commons in 37 years, Mr Johnson seeks the support of MPs in a “meaningful vote” on his new deal but instead they back an amendment forcing him to seek a delay.

Brexit
The “Super Saturday” sitting of the House of Commons (Jessica Taylor/PA)

– October 22 2019

The Prime Minister mounts an attempt to fast-track his Brexit deal through Parliament but puts the plans on ice after MPs vote against his foreshortened timetable.

– October 28 2019

EU leaders agree to a second Brexit “flextension” until January 31 unless Parliament ratifies the deal sooner.

– October 29 2019

Mr Johnson finally succeeds at the fourth attempt in winning Commons support for a general election on December 12.

– December 12 2019

Having campaigned on a promise to “get Brexit done”, Mr Johnson secures a landslide win at the election with an 80-seat majority.

General Election 2019
Boris Jonson after winning and 80 seat majority (Leon Neal/PA)

– January 8 2020

New European Commission president Ursula von der Leyen visits No 10 to warn Mr Johnson the timetable for a post-Brexit trade deal is “very, very tight”. The Prime Minister is clear however there will be no extension to the transition period, which expires at the end of 2020.

– January 9 2020

Mr Johnson gets his Brexit deal through the Commons as the European Union (Withdrawal Agreement) Bill is given a third reading with a majority of 99.

– January 31 2020

A clock projected on the walls of Downing Street counts down the moments to the UK’s departure from the EU at 11pm.

Brexit
Pro-Brexit supporters in the last hours of the UK’s membership of the EU (Andrew Milligan/PA)

– March 2 2020

Mr Barnier and Mr Johnson’s chief EU adviser Lord Frost open formal talks in Brussels on Britain’s future relationship with the bloc, including a free trade agreement.

– March 12 2020

The two sides announce they are suspending face-to-face talks due to the coronavirus pandemic and will explore the options for continuing the negotiations by video conferencing.

– June 12 2020

Cabinet Office Minister Michael Gove formally tells the EU the UK will not sign up to an extension to the transition period, but he backtracks on plans to immediately introduce full border checks with the bloc on January 1.

– September 10 2020

The European Commission threatens the UK with legal action after ministers announce plans for legislation enabling them to override provisions in the Withdrawal Agreement relating to Northern Ireland in breach of international law.

Brexit
Post-Brexit trade talks are hampered by the pandemic (Stefan Rousseau/PA)

– October 16 2020

Mr Johnson says he is halting talks on a trade deal, accusing EU leaders meeting for a summit in Brussels of seeking to impose “unacceptable” demands.

– November 7 2020

Mr Johnson and Mrs von der Leyen agree to “redouble” their efforts to get a deal while acknowledging that significant differences remain over fisheries and the so-called “level playing field” for state aid rules.

-December 4 2020

Lord Frost and Mr Barnier announce in a joint statement the conditions for an agreement had still not been met and negotiations will be put on “pause” to allow political leaders to take stock, with Mr Johnson and Mrs von der Leyen to engage in emergency talks.

– December 9 2020

Mr Johnson and Mrs von der Leyen dine at the European Commission, with talks between the two leaders lasting around three hours and ending in an agreement to have further discussions, but that a “firm decision” should be taken about the future of the talks by Sunday.

Brexit
Boris Johnson and Ursula von der Leyen continue talks in person (Kirsty Wigglesworth/PA)

– December 13 2020

Following a phone call, Mr Johnson and Mrs von der Leyen agree to another extension of talks to “go the extra mile” to find a breakthrough. Mr Johnson says there is a “deal to be done” with the EU but adds the two sides are “very far apart” on key issues and Britain is still ready to trade on WTO terms in the new year.

– December 17 2020

The Prime Minister and European Commission president talk on the phone again to take stock of the discussions, just hours after Mr Gove tells MPs the chances of a deal were “less than 50%”.

The two sides both say progress has been made but there are still “fundamental” differences, with fisheries again a sticking point. Mr Johnson describes the continuing negotiations as being in a “serious situation”, adding an agreement was not likely, with time “very short”.

– December 20 2020

France joins several other European countries in banning travel from the UK, including freight, due to a new coronavirus strain found in Britain, causing the Port of Dover to close. Huge queues of lorries build up on the M20, prompting fears the same could happen in the event of no trade deal being secured.

Brexit
Lorries queue on the A20 to enter the port of Dover in Kent (Gareth Fuller/PA)

– December 21 2020

Transport Secretary Grant Shapps says there is no chance of extending the transition arrangements beyond December 31 because it would “add fuel to the fire” by adding extra uncertainty.

Meanwhile, Mr Johnson updates the country on the travel ban and reveals he has spoken to French President Emmanuel Macron to try to find a resolution, but that they “decided not to speak about Brexit”.

– December 22 2020

An agreement is reached with France to reopen the border, allowing lorry drivers through if they have had a negative Covid test. Mr Barnier briefs EU ambassadors and MEPs and tells them talks are at a “crucial moment”, while Mr Johnson remains in “close contact” with Mrs von der Leyen.

– December 23 2020

Optimism grows throughout the day a deal is about to reached and a Downing Street source says it is “possible, but far from certain”.

– December 24 2020

A post-Brexit trade deal is secured by negotiators from the UK and the European Union. Mr Johnson says the UK had managed to “take back control” as promised in the 2016 referendum.

Mrs von der Leyen says it was a fair and balanced deal, adding “it is time to leave Brexit behind”. Meanwhile, Sir Keir Starmer says Labour will “accept it and vote for it” when the deal with the EU reaches Parliament.

Mr Johnson calls the Queen for an audience during the afternoon, according to the Palace court circular.

– December 26, 2020

The full text of the trade deal is published shortly before 9am, with the document running to up to 1,255 pages.

– December 30, 2020

European Commission president Ursula von der Leyen and European Council president Charles Michel formally signed the agreement, before it was flown from Brussels by the RAF to London where Mr Johnson put his name to it.

MPs and peers approved the trade deal following just one day of debate in both Houses, and in the late hours the Bill received royal assent.

Brexit
Ursula von der Leyen and Charles Michel signing the Agreement on the Withdrawal of the UK from the EU, watched by chief negotiator Michel Barnier (European Commission/PA)

– December 31, 2020

The UK reaches an agreement on a “political framework” to form the basis of a separate treaty with the EU regarding Gibraltar.

– December 31, 2020

The Brexit transition period between the UK and the EU ends at 11pm – 47 years after the UK joined the trading block.

– January 11, 2021

A new insurance card enabling UK travellers to access healthcare in the EU is launched. Global Health Insurance Cards (GHIC) became available as part of the UK’s post-Brexit deal with the bloc.

– February 1, 2021

Hostility to towards port staff from Loyalists prompts Northern Ireland’s Department of Agriculture, Environment and Rural Affairs (Daera) to halt check on animal-based foodstuffs at Belfast and Larne ports.

Daera said the pause was necessary to protect the welfare of its employees after graffiti appeared in the area describing port officers as “targets”.

Northern Ireland unrest
Graffiti on a wall in the Waterside of Derry City (Liam McBurney/PA)

– February 22, 2021

Health certificates on imports of British sausages and mince to Northern Ireland are now required until July 1, when the importation of such products are due to be banned completely.

– February 26, 2021

Northern Ireland’s DUP Agriculture Minister Gordon Lyons orders officials to halt construction of permanent inspection facilities for post-Brexit checks on agri-food goods arriving from Great Britain.

Sinn Fein deputy First Minister Michelle O’Neill brands the move a “stunt”.

– March 1, 2021

The EU Commission announces it expects permanent post-Brexit border control posts to be ready in Northern Ireland by the middle of the year in order to meet the obligations of the protocol.

– March 3, 2021

The UK Government makes the unilateral decision to extend Irish Sea border grace periods on exports from Britain to Ireland.

The first of the light-touch regulation schemes had been due to expire at the end of March, but Lord Frost says the move will allow more time for discussions with the EU.

– March 15, 2021

The EU formally launches legal action against the EU over its move to unilaterally extend post-Brexit grace periods on trace in Northern Ireland.

It states the UK has broken international law and issued proceedings that could see the Government defend itself in the European Court of Justice over the alleged breach of the Northern Ireland Protocol.

– April 15, 2021

Permanent facilities for post-Brexit checks at Northern Ireland ports will not be operating before 2023, Members of Ireland’s Legislative Assembly are told.

The senior official in the Stormont department responsible for the construction said the delay was due to ongoing uncertainty over the volume of regulatory inspections that will be required when grace periods limiting the red tape end.

– April 28, 2021

A “new era” in the UK-European Union relationship begins after MEPs overwhelmingly backed the post-Brexit trade deal by 660 votes to five, with 32 abstentions.

– April 28, 2021

DUP leader and First Minister of Northern Ireland Arlene Foster is ousted over discontent with the party’s Brexit strategy.

The party rank and file lay some of the blame for the emergence of an Irish Sea border at her door.

– May 6, 2021

French fisherman stage a protest off the coast of Jersey following a row over the new licences they are required to obtain to access the waters around the Channel Islands.

Jersey fishing dispute
French fishing vessels staging a protest outside the harbour at St Helier, Jersey (Gary Grimshaw/Bailiwick Express)

HMS Severn and HMS Tamar are deployed in response to fears the French boats could blockade St Helier, while the French maritime authority for the Channel send two police vessels to the area “to ensure the protection of human life at sea”.

Following a day of drama, the flotilla of vessels return to France.

– May 25, 2021

A delegation from the DUP tell Lord Frost the Northern Ireland Protocol must be scrapped.

MP Sir Jeffrey Donaldson says: “Our message was clear and unambiguous, the protocol must go and the Government should take further unilateral action to restore our province’s full and unfettered access to the United Kingdom internal market.”

Democratic Unionist Party meet to ratify new leader
Sir Jeffrey Donaldson led calls for the NI Protocol to be scrapped (Brian Lawless/PA)

– June 9, 2021

The EU threatens to launch a trade war against Britain if it fails to implement checks on goods entering Northern Ireland under the terms of the protocol.

After talks in London ended without a breakthrough, European Commission vice-president Maros Sefcovic said patience with the UK was wearing “very, very thin”.

Brexit Minister Lord Frost refuses to rule out the possibility of the UK unilaterally delaying imposing checks on British-made sausages and other chilled meats due to come into force on July 1.

– June 12, 2021

Speaking at the G7 in Cornwall, Boris Johnson warns Brussels he will not hesitate to take unilateral measures to protect the position of Northern Ireland in the increasingly bitter row over post-Brexit trading arrangements.

G7 Summit
Boris Johnson threatens to act unilaterally in breach of Northern Ireland Protocol (Ben Stansall/PA)

– June 15, 2021

British farms voice their fears that the newly announced free trade deal with Australia will lead to a drop in animal welfare standards and flood the market with cheap, imported meat.

Downing Street says products like cars, Scotch whisky and confectionary will be cheaper to sell to Australia because of the tariff-free agreement, while British farmers will be protected by a cap on tariff-free imports for 15 years.

– June 17, 2021

The EU warns “there is no alternative” to the Brexit arrangements put in place for Northern Ireland, as the UK seeks an extension to temporary measures allowing sausages to cross the Irish Sea.

The UK has formally requests an extension, allowing sausages, burgers and mince to continue being sent from Great Britain to Northern Ireland until September 30.

Fears grow that the UK will unilaterally extend the arrangement, triggering a “sausage war” trade dispute.