Nineteen points separate the sides with the midway point of the campaign on the horizon, meaning very different ambitions for both.
Match preview
After three mid-table finishes since relegation from the Championship in 2019, Ipswich finally look equipped to sustain a proper challenge to get back into the second tier.
It will be far from plain sailing though, as the top of League One looks very competitive at the moment, with the top five all in the mix and in good form.
Kieran McKenna has made his Ipswich side very tough to beat, as a shock defeat to Lincoln City aside, league leaders Plymouth Argyle are the only other side who have beaten the Tractor Boys in League One this season.
Their home form is what has let them down though, as they have dropped points in three of their eight home matches, and when compared to Plymouth, who have won nine from nine at home, there lies the reason why Argyle sit four points clear.
What is keeping them in the title race currently is their supreme away form, as they have picked up four points more than any other side on the road, but they will have been devastated at their last league outing away to Charlton Athletic.
After squandering a 2-0 lead, they were ecstatic when Freddie Ladapo looked like he had clinched the winner to make it 3-2 on 90 minutes, before Sam Morsy made it 4-2 moments later to surely seal the win.
However, they inexplicably allowed Charlton to score 96th and 99th-minute goals to bring the game back to 4-4, and throw away two potentially vital points in the process.
Meanwhile, Cheltenham have given their fans very little to get excited about so far this season.
Losing at home to a side in the seventh-tier relegation zone, Alvechurch, last weekend in the FA Cup was a particularly harrowing experience for the supporters, as they were the lowest-ranked side to progress to the second round.
That result somehow managed to outdo the embarrassment of their exit from the League Cup earlier this season too, when Exeter City came to Whaddon Road and won 7-0.
They may not be in imminent danger, sitting four points above the relegation zone with a game in hand, but their 13 goals in 16 league games has not exactly set the league alight.
Their loyal travelling support have not seen much joy either, as no side has picked up fewer points (five) or scored fewer goals (three) than they have on the road, even if they have played a game or two fewer than some sides.
After a slight upturn in fortunes at the start of October, five defeats in their last seven and just four goals scored in that time has not been good enough, and has unsurprisingly led to a drop down the table.
Ipswich Town League One form:
W
W
L
W
W
D
Ipswich Town form (all competitions):
L
L
W
W
D
W
Cheltenham Town League One form:
W
L
L
L
W
D
Cheltenham Town form (all competitions):
L
L
L
W
D
L
Team News
Ladapo should be able to force his way into the Ipswich starting lineup after a goal in the cup last weekend saw him extend his tally to four goals in three games.
He has not been able to nail down a regular starting spot in the side on a consistent basis this season, but his recent form should offer him the chance.
Injuries to attackers Sone Aluko and Gassan Ahadme offers an even greater opportunity for those up front to make an impact.
Lee Evans and Greg Leigh remain the other first team absentees for Ipswich.
Dan N'Lundulu started as a sub for Cheltenham on his return from injury last weekend but still played nearly an hour as his side chased to get back in the game from the outset.
With N'Lundulu fit again up front, George Lloyd may drop back to the bench here, as he is still goalless this season after 16 appearances.
Getting Alfie May back to full fitness will be of utmost importance though, as last season's 26-goal man has missed over a month injured.
A 22-minute cameo in the cup last week was positive progress for the 29-year-old striker.
Ipswich Town possible starting lineup:
Walton; Donacien, Woolfenden, Edmundson; Burns, Ball, Morsy, Davis; Chaplin, Ladapo, John-Jules
Cheltenham Town possible starting lineup:
Southwood; Jackson, Long, Taylor, Freestone, Williams; Sercombe, Perry, Olayinka, Broom; N'Lundulu
We say: Ipswich Town 2-0 Cheltenham Town
Ipswich have made light work of most sides in the bottom half this season, and with just two defeats all season, a side as out of form as Cheltenham should be an obstacle they can hurdle.