While the birth of the Old Xaverians Football Club was still nearly a quarter of a century away, the first association with amateur football came in 1899, when Xavier College (as St Francis Xavier) entered a team in the Metropolitan Junior Football Association (later the MAFA, then VAFA).

It was a doomed connection, as the Xaverian reported in language that reflected the spirit of the times.

"It is a hard task to fill a football list with matches against teams of a sufficient degree of respectability. Teams at times have visited the College composed of men, who would be more in their element were they in a less gentlemanly atmosphere. It was to obviate this that we tried and succeeded in gaining admittance to the M.J.F. Association. We played one or two matches and some practice matches in this Association; but we were invariably beaten. We had no chance - boys played against men, the result was evident from the beginning. Repeated defeats caused our boys gradually to lose heart. The committee were consulted and thinking "discretion the better part of valour" we reluctantly resigned our place in the Association. But this time had not been wasted. These matches had shown our fellows their weak points, and in the practice many faults were corrected that had not else been noticed. Great improvement was noticeable in the the quick passing, and the increased absence of selfish play was soon evident."

The Xaverian makes special note of the game against Cumloden College: "In this match we had rather bad luck. The umpiring was, to say the least of it, not too fair. This, the Cumloden team, who are a right decent lot of fellows (in the words of one of ours) admitted."  

Old Boy, speaking of this match said "Both teams were keen to win from start to finish, and though the umpiring of Mackay was hardly strict enough, the game itself, both in tone and eagerness, was a good example of what these matches should be."