For the 1986-87 campaign Sholing Sports became founder members of the newly formed Wessex League, and enjoyed a steady debut season as they reached the finals of the Southampton Senior Cup and the inaugural League Cup. The next few years saw the club continue to hold their own but in a more professional environment their fortunes gradually declined - not helped in the early 1990s by increasing uncertainty over their Birch Lawn ground, caused mainly by financial problems at the adjacent Social Club.