Two second half goals from Tom Naylor and Brett Pitman secured a 2-1 win for Portsmouth at Fratton Park after Jordy Hiwula had given City a first half lead.
The first chance of the game fell to the home side. A corner was whipped in to the box by Pompey and Burge failed to deal with it, but Tom Davies was on hand to clear the ball off the line.
However, it was City who took the lead. Superb work from Bright Enobakhare saw him break forward and slip the ball into the path of Jordy Hiwula who fired past MacGillivray to put the Sky Blues ahead.
Luke Thomas then had a golden opportunity to double the advantage. A wonderful ball from Kelly set the winger away and he rounded MacGillivray, but his shot from a tight angle was well blocked on the line by a Portsmouth defender.
Portsmouth were beginning to get a foothold in the match and Brett Pitman’s volley had to be deflected behind for a corner. From that corner, Tom Naylor probably should have levelled the tie, but he headed over from close range.
Pitman had another opening moments later. The Pompey captain picked up the ball just outside the area, however his curling shot rose harmlessly over the bar.
Bakayoko went close with a header just before half time. Tom Davies moved forward with the ball and cross for Baka, but his header went over the bar leaving the Pompey goalkeeper untroubled.
Liam Kelly had the final chance in first half stoppage time. The midfielder picked the pocket of Ben close and let fly from range, but his effort cleared the crossbar as City went in a goal up at the break.
It was Portsmouth who had the first chance of the half ten minutes after the restart. A cross from Jamal Lowe found the left back in space at the back post, but he volleyed wide of Burge’s goal.
James Vaughan had a great chance to draw the home side level midway through the half. A Pompey attack resulted in Thompson crossing for Vaughan, but he failed to get a clean connection with his header, and it flew wide.
Portsmouth did draw level in the 66th minute through Tom Naylor. A corner was whipped in and Naylor rose highest to head home the equaliser.
Luke Thomas had a chance to put the Sky Blues ahead after 72 minutes. A smart ball from Enobakhare put Thomas in, he lofted the ball over the keeper, but it went the wrong side of the post.
However, Pompey responded with a chance of their own. Jamal Lowe picked up the ball on the edge of the box and looked to curl a shot in to the far corner, but it went wide and out for a goal kick.
Jamal Lowe was proving a constant threat for the home side and he tested Burge in the 82nd minute. Lowe ran at the City back line and got a powerful shot away which Burge had to tip round the post.
Pompey grabbed a second from the resulting corner. It missed everyone and was recycled back in to box by Close and was eventually smashed in to the net by Brett Pitman to give the home side the lead after City failed to defend the cross.
That was the final action of the game as City slipped to a 2-1 defeat in Hampshire.
CCFC XI: Burge (GK), Mason, Davies (Willis 74’), Kelly, Hiwula, Hyam, Sterling, Bakayoko, Thomas (Chaplin 74’), Enobakhare, Shipley (Wakefield 85’).
Unused Subs: Addai (GK), Ponticelli, Westbrooke, McCallum.
Portsmouth XI: MacGillivray, Brown, Clarke Burgess, Naylor, Pitman (Walkes 90'), Hawkins (Vaughan 45’), Lowe, Thompson, Evans (Curtis 45’), Close.
Unused Subs: Bass (GK), Soloman-Otabor, Morris, Haunstrup.
Yellows: Burge 57’,