Arsenal Draws Roy Keane, Ipswich Town in Carling Cup Semi

You may recall Roy Keane from his days at Manchester United... Pic via Daily Mail.

Arsenal advanced to the Carling Cup Semi-Final yesterday with their 2-0 win over Wigan Athletic. The drawing for the next round was held this evening after Birmingham's win over rival Aston Villa and Ipswich Town's 1-0 win over West Brom.

Ipswich Town was drawn first and Arsenal was drawn second in the drawing, meaning that the Gunners will face off against the Championship side in the two-legged semi-final. With Ipswich being drawn first, they will host the first leg at Portman Road on either January 11 or 12. The second leg, which will be played at the Emirates, will be either January 25 or 26. The away goals rule is in effect in this tie.

Arsenal have not played Ipswich Town since the East Anglian side was relegated in 2001/02, a year in which Arsenal won both league fixtures 2-0. The Gunners were knocked out of the League Cup by Ipswich Town the year before that, 2-1, at Highbury on an 89th minute winner from James Scowcroft.

But, the most intriguing element of the tie is Ipswich's manager Roy Keane, once captain of Manchester United from 1997 to 2005, during the height of their rivalry with Arsenal. Keane had a particular rivalry with Patrick Vieira (pictured), which once escalated to a heated argument in the tunnel before a match at Highbury caught live on television.

Arsenal last reached the Carling Cup Semi-Final in 2007/08, but we're going to pretend the second leg of that tie didn't happen. Arsenal last won the League Cup in 1993 when they beat Sheffield Wednesday 2-1.