The January transfer window is often used for teams that desperately need additions, whether they are attempting to get promoted or in the midst of a relegation battle.

However, sometimes these ‘panic-buys’ can turn out to be shrewd pieces of business – here we look at Leyton Orient’s top five January signings of all time.

5. Jonathon Tehoue

Joining the O’s in January 2010, Tehoue was best known for his late goals, having scored nine goals after the 85th minute of various matches during his time at the club.

His most famous moment would be his late equaliser against Arsenal in the FA Cup Fifth Round, earning Orient a replay at the Emirates Stadium in 2011.

4. Charlie Daniels

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Having originally joined the O’s on loan for the 2007/08 season, Daniels re-joined the club in January 2009 after being released from Tottenham Hotspur.

In his second spell with the club, Daniels amassed 138 appearances in all competitions, and was a stalwart in League One before joining AFC Bournemouth in November 2011.

3.  Josh Coulson

Spending the first half of the season on loan from Cambridge United, Coulson made the move permanent in January 2018.

He quickly became a fan favourite at the O’s – Coulson made 47 appearances in the 2018/19 National League title-winning season, and was made first-team captain for the following season.

2. John Mackie

Joining the club in January 2004 from Reading, Mackie soon established himself at the back besides academy graduate Gabriel Zakuani. Mackie made 135 appearances during his four years with the club, and was captain of the side that won automatic promotion to League One in the 2005/06 season.

Before we get to number one, an honourable mention goes to Harry Kane, who is probably the most famous ex-Orient loanee. He spent the second half of the 2010/11 season on loan in East London scoring five goals in 18 matches.

1. Dean Brill

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Joining the club initially as a goalkeeping coach in 2017, Dean Brill was brought into the first-team squad by then-manager Justin Edinburgh to be the club’s first-choice goalkeeper.

He played every single minute of the following league season, and equalled the club record for most clean sheets with 24. Brill retired in January 2020 following a succession of hamstring injuries.