On Saturday the two sides met in the league down at White Hart Lane with the Wanderers securing all three points thanks to goals from Radhi Jaidi and Henrik Pedersen either side of a Robbie Keane strike for Spurs.
Tomorrow could see a number of changes on both sides as last season's finalists Bolton and the 1999 winners Spurs look to make progress in the competition.
Whenever the two teams meet in the League Cup it is never a dull affair. In the 1996-1997 season as Bolton headed for promotion to the Premiership they beat a strong Spurs team 6-1 at Burnden Park with John McGinlay helping himself to a hat trick.
A few years later in the winter of 2001 it was the turn of Tottenham to go on the goal spree, current Bolton striker Les Ferdinand then of Spurs like McGinlay a few years earlier helped himself to a hattrick in a 6-0 demolition.
Ferdinand is one of a number of names who the Bolton boss Sam Allardyce is set to utilise tommorow with former Real Madrid duo Fernando Hierro and Julio Cesar also set to come into contention. International players such as Khalilou Fadiga, Tal Ben-Haim and Blessing Kaku will be pushing for places in the team.
Spurs boss Jacques Santini is also likely to use the game as an opportunity to rest a number of Premiership regulars with Kasey Keller set to deputise for Paul Robinson in goal. Also coming into contention are Swiss midfielder Reto Ziegler and defender Goran Bunjevcevic. Mauricio Taricco returns to the Spurs squad and could replace Johnnie Jackson.
In the past Bolton have been criticised for fielding "weakend" teams but a squad boasting the likes of Ferdinand, Fadiga, Hierro, Ben-Haim and Cesar can hardly be considered as being disrespectful to our opponents. I am sure that both sides will go out and make it a good contest no matter which team is chosen.
LAST TIME OUT (LEAGUE CUP)
11/12/2001 TOTTENHAM HOTSPUR 6 BOLTON WANDERERS 0
PLAYED FOR BOTH
Chris Armstrong
Gudni Bergsson
Chris Fairclough
Les Ferdinand
George Hunt
Don McAllister
Neil McNab
Ian Moores