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Saturday's League One clash will be the 100th time Wanderers have faced off against Portsmouth.
The Whites have a record of 42 wins, 22 draws and 35 defeats against Pompey but haven’t won in the fixture in over a decade.
From five-goal thrillers to late drama, here are some of Bolton’s most memorable wins from over the years.
Portsmouth 2-3 Wanderers (September 12, 2009)
The Whites edged a five-goal thriller when the sides met at Fratton Park in the 2009/10 Premier League season.
Tamir Cohen put the visitors in front with a powerful strike after 13 minutes but Popmey hit back through Younes Kaboul’s header.
Bolton regained the lead on the stroke of half time through Matty Taylor’s penalty but the hosts drew level again, this time through Kevin-Prince Boateng.
Gary Cahill headed home a dramatic winner in the dying moments to ensure Wanderers would return to the North West with all three points.
Wanderers 2-1 Portsmouth (December 20, 2008)
The Whites got off to a dream start when the sides faced off at the UniBol in late 2008, scoring twice in the first three minutes.
Matty Taylor opened the scoring after lifting the ball over his man and firing past David James, before Ricardo Garnder added a second with another thumping volley.
Bolton had enough chances to kill the game off as Kevin Davies’ header was cleared off the line before Gretar Steinsson was denied by the woodwork.
Peter Crouch pulled one back for the visitors, who survived a nervy final few minutes to secure the victory.
Wanderers 3-2 Portsmouth (December 30, 2006)
The Whites won another five-goal thriller against Pompey in late 2006 following an entertaining clash at the UniBol.
The visitors took the lead after just 72 seconds when Taylor found a way past Jussi Jaaskelainen, but Bolton hit back through Abdoulaye Faye on the half-hour mark.
After the break, the hosts seized control of the match thanks goals from Ivan Campo and Nicolas Anelka.
Andy Cole pulled one back at the death but it wasn’t enough to prevent a fifth successive league win for Sam Allardyce’s men.
Wanderers 2-0 Portsmouth (September 16, 2000)
The Whites recorded a 2-0 victory against Pompey back in September 2000 but it wasn’t as straightforward as the scoreline suggests.
Bolton struggled to break down the visitors’ stubborn defence in the early stages, while Shaun Derry missed a big opportunity at the other end.
But the hosts managed to break the deadlock on the stroke of half time when Dean Holdsworth found space in the box and rifled home from 10 yards.
And Michael Ricketts wrapped up the result with five minutes to go, slotting home after getting on the end of Bo Hansen’s threaded through ball.
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Saturday's League One clash will be the 100th time Wanderers have faced off against Portsmouth.
The Whites have a record of 42 wins, 22 draws and 35 defeats against Pompey but haven’t won in the fixture in over a decade.
From five-goal thrillers to late drama, here are some of Bolton’s most memorable wins from over the years.
Portsmouth 2-3 Wanderers (September 12, 2009)
The Whites edged a five-goal thriller when the sides met at Fratton Park in the 2009/10 Premier League season.
Tamir Cohen put the visitors in front with a powerful strike after 13 minutes but Popmey hit back through Younes Kaboul’s header.
Bolton regained the lead on the stroke of half time through Matty Taylor’s penalty but the hosts drew level again, this time through Kevin-Prince Boateng.
Gary Cahill headed home a dramatic winner in the dying moments to ensure Wanderers would return to the North West with all three points.
Wanderers 2-1 Portsmouth (December 20, 2008)
The Whites got off to a dream start when the sides faced off at the UniBol in late 2008, scoring twice in the first three minutes.
Matty Taylor opened the scoring after lifting the ball over his man and firing past David James, before Ricardo Garnder added a second with another thumping volley.
Bolton had enough chances to kill the game off as Kevin Davies’ header was cleared off the line before Gretar Steinsson was denied by the woodwork.
Peter Crouch pulled one back for the visitors, who survived a nervy final few minutes to secure the victory.
Wanderers 3-2 Portsmouth (December 30, 2006)
The Whites won another five-goal thriller against Pompey in late 2006 following an entertaining clash at the UniBol.
The visitors took the lead after just 72 seconds when Taylor found a way past Jussi Jaaskelainen, but Bolton hit back through Abdoulaye Faye on the half-hour mark.
After the break, the hosts seized control of the match thanks goals from Ivan Campo and Nicolas Anelka.
Andy Cole pulled one back at the death but it wasn’t enough to prevent a fifth successive league win for Sam Allardyce’s men.
Wanderers 2-0 Portsmouth (September 16, 2000)
The Whites recorded a 2-0 victory against Pompey back in September 2000 but it wasn’t as straightforward as the scoreline suggests.
Bolton struggled to break down the visitors’ stubborn defence in the early stages, while Shaun Derry missed a big opportunity at the other end.
But the hosts managed to break the deadlock on the stroke of half time when Dean Holdsworth found space in the box and rifled home from 10 yards.
And Michael Ricketts wrapped up the result with five minutes to go, slotting home after getting on the end of Bo Hansen’s threaded through ball.
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