Arsenal beat Bolton 1-0 in the sixth round en route to winning the Cup in the 2004-05 season but Bolton won last season's fourth round tie by the same score at the Reebok Stadium.
They have become something of a bogey side for Arsenal, having lost only once to the north London side in their last seven league and cup meetings.
They now face each other again at the Emirates Stadium at the end of the month although Bolton chairman Phil Gartside said he wished Bolton had been drawn at home.
"It would have been nice to have been at home," he told Sky Sports News. "But any game against Arsenal is a big game for anybody. We've had a great record against Arsenal in the last few years and done it on merit but I don't want to say any more about that and put the dampeners on it."
Arsenal reached the last 32 after knocking out holders Liverpool 3-1 at Anfield on Saturday, while Bolton won 4-0 at third division Doncaster Rovers.
Manchester United, who beat Aston Villa 2-1 on Sunday, face another all-Premier League tie after being drawn to play Portsmouth at Old Trafford where Portsmouth have not won against United since 1957.
Chelsea were handed another relatively easy home tie after beating fourth division Macclesfield Town 6-1 on Saturday. They now face third division promotion hopefuls Nottingham Forest, who knocked out Premier League Charlton Athletic 2-0.
Chelsea last played Forest in 2000 when they beat them 2-0 in an FA Cup fourth round tie and went on to win the FA Cup in the last final at the old Wembley Stadium.
This year's final on May 19 is expected to be the first back at the new Wembley after six years in Cardiff.
Third Division Swansea City's reward for their 3-0 win at Premier League Sheffield United is an away tie at either second division Ipswich Town or fourth division Chester City who drew 0-0 at Chester on Saturday.
West Ham United and Watford can both put their relegation worries to one side for the afternoon when they meet in the only other definite all-Premier League tie at Upton Park while Wolverhampton Wanderers could face West Bromwich Albion in a Black Country FA Cup derby for the first time since 1961-62 if Wolves win their replay against Oldham Athletic.
Wolves have beaten their midland rivals only once in 10 FA Cup meetings going back to 1886.
The matches will be played on the weekend of January 27-28.
