The two sides finished fifth and fourth in the table respectively, with the visitors five points better off than their hosts despite a slow end to the regular season.
Match preview
Bolton Wanderers head into the League One playoffs on the back of a positive season under Ian Evatt's management, having improved on last season's ninth-placed finish while also winning the EFL Trophy, having thrashed third-tier champions Plymouth Argyle 4-0 in the final at Wembley at the beginning of April courtesy of goals from Kyle Dempsey, Dion Charles, Elias Kachunga and Gethin Jones.
On the league front, the Trotters have sat in the top six since March and they went a long way towards confirming a playoff spot with a six-game unbeaten run between mid-March and mid-April, picking up 12 points along the way thanks to 1-0 victories over Exeter City, Oxford United and Shrewsbury Town.
That positive streak was halted by a disappointing 1-0 defeat at home to Accrington Stanley, leaving Evatt's men on 75 points heading into the final two matches of the regular season, but they were still able to confirm a playoff place in the following encounter away at Fleetwood Town at the end of April, as a Promise Omochere own goal had them ahead inside 20 minutes before Kyle Dempsey wrapped up a 2-0 victory 12 minutes from time.
Such a result meant the Lancashire outfit headed into the final day with some pressure lifted and only with fifth place to fight for with Derby County, who sat two points behind, and the Trotters set up their playoff meeting with Barnsley with a 3-2 win in a dramatic contest away at Bristol Rovers, as Shola Shoretire, Dan N'Lundulu and Aaron Morley all got on the scoresheet.
Now feeling positive on the back of those closing victories, making it three from their last four league matches, Bolton Wanderers will aim to get on the front foot in their home leg and put a lead on the board before heading to Barnsley next week.
Their visitors arrive hoping to take a step closer to making an immediate climb back to the Championship following their relegation last term, having not dropped out of the playoff spots in England's third tier since December.
Largely thanks to a strong run of form between January and March, in which they put together a 12-game unbeaten run including 10 victories, before wrapping up their playoff place with wins over Shrewsbury Town, Forest Green Rovers and Oxford United in April, Michael Duff's side finished in fourth spot with 86 points on the board.
That is despite a slow end to the regular campaign for the Reds, who have failed to pick up three points from any of their last three league outings, firstly suffering a 4-0 beating at home to second-placed Ipswich Town, with fourth place confirmed at that stage.
The Yorkshire outfit then travelled to relegation-threatened MK Dons and came away with a point from a dramatic 4-4 draw, as they trailed 4-1 heading into the final 20 minutes, only to harm their hosts and draw level thanks to James Norwood's second goal of the game and a Max Watters brace, before hosting Peterborough United on the final day on Sunday and falling to a 2-0 defeat which saw their visitors climb into the playoff spots courtesy of goals from Jonson Clarke-Harris and Jack Taylor.
While they may not be too disheartened by those results, given that little was on the line in their three games prior to the playoffs, Duff's men will be keen to return to their best on Saturday and will go in search of a positive result in Lancashire to gain the edge in the semi-final tie before their home leg next week.
Bolton Wanderers League One form:
W
D
W
L
W
W
Barnsley League One form:
W
D
W
L
D
L
Team News
With the playoffs in mind, Ian Evatt made several rotations to his Bolton squad at the weekend, and he should revert back to his strongest side on Saturday, albeit with full-back Gethin Jones being a doubt after he came off in the first half of the Bristol Rovers game, while Jack Iredale and Jon Dadi Bodvarsson also remain sidelined.
Key centre-back Ricardo Santos has returned to contention after his own injury layoff, though, and after playing the first half of Sunday's game, he is bound to start at the heart of a back three alongside Eoin Toal and George Johnston.
At the other end of the pitch, Dion Charles will come back in to lead the line, having netted 20 goals in all competitions so far this season, while Victor Adeboyejo is the most likely to join him up front, ahead of the likes of Shola Shoretire and Cameron Jerome.
Barnsley defender and captain Mads Andersen missed the final two matches of the regular season, and he is unlikely to be fit in time to return from the outset on Saturday, with Duff instead expected to deploy an unchanged back three of Jordan Williams, Bobby Thomas and Liam Kitching for the first leg.
Indeed, the side he reverted back to on Sunday could be the one that starts at the University of Bolton Stadium, with James Norwood and Devante Cole likely to be the preferred strike pairing having netted 11 and 15 league goals respectively this term.
Further back, Luca Connell has been a key man in midfield since his summer arrival from Celtic, and he will again feature in the engine room, likely alongside Herbie Kane and Adam Phillips.
Bolton Wanderers possible starting lineup:
Trafford; Toal, Santos, Johnston; Bradley, Sheehan, Lee, John; Dempsey; Adeboyejo, Charles
Barnsley possible starting lineup:
Isted; Williams, Thomas, Kitching; Cotter, Phillips, Connell, Kane, Cadden; Norwood, Cole