The Robins suffered late heartbreak in a 3-1 defeat to Charlton Athletic on Tuesday evening at the Completely-Suzuki Stadium.
Daniel Kanu opened the scoring for the visitors before an inspired moment from substitute Jordan Thomas led to Liam Sercombe’s leveller for Town.
But a pair of late goals from Tyreeq Bakinson and Alfie May ensured the Addicks left Cheltenham with all three points.
“It was an end-to-end game and we’ve come out of it disappointed,” said manager Darrell Clarke post-match.
“It's a disappointed changing room but like I said to my players in there, they’ve given me absolutely everything since I’ve come through the door.
“It's one of those nights where it wasn’t our night and we’re disappointed because once we got the equaliser, we might go onto win it but a couple of sloppy goals has cost us the game.”
The game started slowly until the 19th minute when Conor Coventry’s threaded pass broke the Robins defensive line allowing Tennai Watson in behind down the right hand side.
His square ball found Kanu in the area who kept his cool and steered past Luke Southwood to put the visitors in front.
The Robins responded as Tom Bradbury flicked a header just wide before Sercombe’s neat pass found George Lloyd, but his shot was well blocked by Macaulay Gillesphey.
The Addicks roared back and had a flurry of chances, as May’s inswinging corner needing tipping over by Town’s number one before Southwood beat another of the striker's shots away before May dragged the rebound wide.
May would come close on two more occasions before the first half came to an end as a lobbed shot nestled on the roof of the net before a drive from outside the box was once again denied by a busy Southwood.
The Robins began the second half with a renewed energy as Elliot Bonds dragged his shot wide before the captain Sean Long fired one narrowly past the other post moments later.
A moment of magic came on the 70th minute mark as the Robins managed to pull themselves level.
Substitute Thomas danced his way past two Charlton defenders before his shot was saved by Harry Isted but Sercombe was on hand to tap into an empty net for the equaliser.
It was Town who looked the more likely to snatch a late winner but a cruel blow was dealt to the hosts with four minutes of normal time remaining.
Substitute Bakinson brought the ball down inside the area before squeezing a shot past Southwood despite the goalkeeper getting a strong right hand to the effort.
And seconds before added time the result was put beyond doubt as May walked the ball into an empty after an unfortunate slip from Tom Pett.
CHELTENHAM TOWN (3-5-2): Southwood; Long (c), Davies, Bradbury; Kinsella, Sercombe, Pett, Bonds (Thomas 60), Ferry (Smith 25); Taylor (Keena 76), Lloyd. Subs not used: Pardington (Gk), Shepherd, Sloggett, Harrop.
CHARLTON ATHLETIC (3-5-2): Isted; Edmonds-Green (Jones 65), Thomas (Hector 90), Gillesphey; Watson, Anderson (Bakinson 79), Coventry, Dobson (c); Kanu (Ladapo 79), May. Subs not used: Maynard-Brewer (Gk), Campbell, Asiimwe.
REFEREE: S Jackson
ATTENDANCE: 4,392 (629 from Charlton)
