The Robins secured automatic promotion last night following a 1-1 draw with Carlisle.
With two matches remaining, Michael Duff s side cannot mathematically be caught by fourth-placed Morecambe - and will return to the third tier for the first time since 2009.
It represents a fine achievement for Cheltenham, who suffered no hangover after losing to Northampton in the play-off semi-finals last campaign.
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Town currently sit top of League Two and could clinch the title on Saturday with a win at Newport if second-placed Newport lose to Harrogate and third-placed Bolton drop points against Exeter.
Duff secured six promotions during his playing days with Cheltenham and Burnley, reaching the Premier League with the latter on two occasions.
However, masterminding the Robins’ promotion was a better feeling.
Duff told Gloucestershire Live: ‘It’s better. As a player you are a small cog in a big wheel really, but to be the leader of this group after the disappointment of last year.
‘The amount of times we’ve been questioned over the last two years and historically the club has struggled at the wrong end of the table. I am immensely proud to be in charge of this mob. Board, players, staff and supporters have all been brilliant.
‘I said it from the start, you want to leave the club in a better state than you found it and it’s taken a lot of hard work. It doesn’t happen overnight, Grant McCann will tell you that now at Hull, but you want a chance and I thought I’d be given a chance.
‘If I am being brutally honest, did I think I could get Cheltenham Town promoted? No. I didn’t think the budget, or the facilities would allow it, but we got onto something. I found at the start, the group was good and it’s so powerful, particularly at this level.’
Should Pompey fail to secure League One promotion with two games remaining, they'll travel to Whaddon Road for a league fixture for the first time since the 2016-17 campaign.
Paul Cook's side memorably claimed the fourth-tier crown on the final day with a 6-1 defeat of Cheltenham at Fratton Park.
The Blues did visit Town in the Papa John's Trophy this term, with Jordy Hiwula notching a double and Haji Mnoga on target in a 3-0 win.