At the time of its opening, The Dell was considered to be the most compact ground in the country — the players got their first taste of their new home when they participated in a sports meeting there on 27 August 1898.

[1] Determined to build on their success of the previous season, the club signed several new players during the summer of 1898, including five present or former internationals — Scotsmen Geordie Dewar, Peter Meechan and John Robertson and Englishmen Jack Robinson and Harry Wood.

Towards the end of the first-half, Arthur Chadwick accidentally caught Brighton's centre-forward Willie McArthur on the chin with a high kick.

[1] Bristol City were playing their second season in the Southern League having finished as runners-up in 1897–98, and were undefeated at their St John's Lane ground.

Early in the game, England international goalkeeper Jack Robinson damaged his right hand, attempting to prevent a goal from Billy Langham, City's outside-right.

Robinson played on in considerable pain but was unable to prevent the ball entering the goal off the cross bar from a Langham free-kick; thus the first half ended with Bristol City having a 2–0 lead.

[5] For the second half, Southampton made a tactical change, switching Roddy McLeod to centre-forward with Duncan McLean moving to inside-right and within 12 minutes of the restart the scores were level, after long shots from Arthur Chadwick and Jock Robertson, the latter going in after a "gentle hint" from Harry Wood turned the ball past goalkeeper, Hugh Monteith who had come too far out of his goal.

In Round One, they met fellow Southern League side, New Brompton, with Abe Hartley scoring the winner 20 minutes from time.

[1] This set up the first FA Cup match to be played at The Dell, against Derby County of the Football League First Division, who were the beaten finalists from the previous year.

[1][8] Two days later, Southampton entertained Rangers, the newly crowned Scottish Football League champions, with the Saints going down by the single goal.