[Note: This page is still a work in progress. This is my first entry, so additional editing by more experienced users is appreciated especially with regards to formatting. Do not deadpool yet]

Overview

In the world of Association Football, the Transfer Window is a period during the year in which football clubs are allowed to trade players. There are two distinct windows, the dates of which are fixed by the football governing body of each country (e.g. The FA in England). The most well-known period is the English transfer window, which occurs on the following dates: 9 June – 1 September and 1–31 January.^[1]

The transfer Deadline Day is the last day of the window. This is usually one of the busiest days of the window, generating a flurry of transfers, often because a number of interdependent transfers are completed resembling a housing chain, generating much media interest. The deadline day is accompanied by round the clock reporting by sports journalists and websites such as Sky Sports and Eurosport, and on social media such as Facebook and Twitter.

Recurring Themes in Each Deadline Day

Due to the heavy news coverage that the Deadline Day receives together with the popular nature of sportspersons, many events that happen on each deadline day have become well-known amongst the football community. These are accompanied by a meme-like spread on Facebook, Twitter and other social networking sites.

Jim White / Sky News Reporting

Jim White is a Scottish television presenter that works for Sky Sports. He is best known for his round-the-clock presenting marathon on the transfer deadline days.^[2] Because of this, the days (1st September and 31 January) are sometimes affectionately referred to as “Jim White day” by football fans.

Jim White’s coverage is accompanied by several field reporters giving the latest news from outside the main football clubs’ headquarters. These are often surrounded by the fans of the respective clubs. Due to the live nature of the reports, many notable moments have occurred, some of which are listed below.

It's gone too far now: https://t.co/R4df41E6KP
— James Dall (@JamesDallESPN) September 1, 2014

Harry Redknapp Leaning Out of the Window

Harry Redknapp is an English football manager. He is currently the manager of Premiership side Queens Park rangers but has managed other big-name clubs such as Portsmouth and Tottenham.^[3] He is usually one of the busiest men on the transfer deadline day, receiving notable media attention. He is regularly stopped by Sky Sports reporters waiting for him outside the parking lot of his club, and has to lean out of his car window in order to answer. This has become synonymous with Deadline Day and is accompanied by several image macros and videos shared on sites such as Facebook, Twitter, and Youtube.^[4]

Harry Redknapp snubs Cotterill https://t.co/2VdEbBId8J
— Samuel Luckhurst (@samuelluckhurst) September 1, 2014

Arsene Wenger

Arsene Wenger is the manager of Premier League side Arsenal.^[5] Due to his job managing one of the most popular football clubs in the world, his dealings on deadline day are the target of several image macros, either by happy / disappointed Arsenal fans or by rival teams’ fans sharing some banter.

Surprising / Shock Deadline Day Deals

Being the last day of the transfer window, many teams often rush to sign some heavily-needed players. Deadline Day deals are often done in a desperate manner (most deals are concluded only hours before the 11pm deadline, with some teams having to request a special extension), and this often results in clubs grossly overpaying for a player’s services or signing a player of a lower calibre than expected. These deals are covered heavily in the press, and are the subject of several image macros on sites such as Facebook, Twitter and other football-related forums.^[6]

Examples of major Deadline Day Deals include:
Marouane Fellaini (September 2013) Everton to Mancehester United
Mesut Oezil (January 2014) Real Madrid to Arsenal
Fernando Torres (September 2014) Chelsea to AC Milan
Radamel Falcao (September 2014) AS Monaco to Manchester United^[7]
Danny Welbeck (September 2014) Manchester United to Arsenal
Tom Cleverley (September 2014) Manchester United to Aston Villa

LVG: "Guys, I'm gunna sign Falcao." Rooney: "Wow, nice one boss." RvP: "Wait.. Radamel Falcao?" pic.twitter.com/zzHVE4vBSm
— Football Funnys (@FootballFunnys) September 1, 2014

Wayne Rooney on hearing Falcao will be earning £346k a week. #transferdeadlineday pic.twitter.com/XH0quErbpD
— BetVictor (@BetVictor) September 1, 2014