Town's U18 side fell to a 2-1 defeat against their Chelsea counterparts at Playford Road on Saturday morning.
Town were without the injured Lewis Ward and Kurt Robinson, as well as striker Jordan Rhodes who has gone on loan to Oxford United.
The young Blues had the best chance of the first-half when striker Jack Ainsley somehow failed to convert from a few yards out after excellent play on the right from Joe Clemo.
Town took the lead on the half-hour mark when Scottish defender Paul Watson rose highest at the back post to score his first goal for the U18 side.
Chelsea controlled the majority of the second-half, and they grabbed an equaliser on 57 when French striker Gael Kakuta slotted the ball home after neat build-up play from Jacob Mellis.
Kakuta and Mellis both squandered good opportunities for the visitors, whilst Town midfielder Curtley Williams saw a looping header strike the Chelsea bar.
The visitors scored what proved to be the winner on 64 when Italian Fabio Borini finished well after a through-ball from Tom Taiwo had caught Town's defence out.
Town U18s: Plummer, Clemo, Roe, C Williams, Watson, Smith, Murphy (Lambe 71), Reason, Ainsley, Calver (Barrett 57) and Fenn (Hyam 57). Unused: Traveller and Clark.
Chelsea U18s: Taylor, Ahamed, Ofori-Twumasi, Bruma, Gordon, Taiwo (Philliskirk 67), Mellis (Tabor 87), Hibbert, Burini, Kakuta and Nielsen (Phillip 61). Unused: Saville and King.