The earliest record of Penn Street Cricket Club is from 1852, from segments of newspaper clippings found by Bob Asprey who was looking into the history of Holmer Green Cricket Club for their Centenary.
In my research I have found these three matches in 1852...
1. Chalfont St Giles (45 & 33) lost to Penn Street (40 &72) (Bucks Chronicle & Bucks Gazette 24/07/1852).
2. Wooburn (55 & 19) lost to Penn Street (30 & 45 for 4 (BC&BG 11/09/1852)
3. Penn Street (60 & 23) beat Wooburn (30 & 16) (BC&BG 25/09/1852).
Furthermore, this also from BC&BG 11/09/1852....
On Saturday last, a single-wicket match was played on Holmer Green, between two gents of that club and two of the Penn Street, which ended in the favour of the latter gents, as the score will show:-
Penn Street - Fenn b by Lee, 5; b by ditto 9-14; Fisher b by ditto 0; b by ditto 2-2.
Holmer Green - Ayres run out 0; b by Fenn 1-1; Lee c by ditto 0; st by ditto 4-4.
Penn St. won by 9 runs.
We also have the record pictured, a newspaper cutting from 1884 of a game between Penn Street and Holmer Green.
We will do our best to get back to you as soon as possible.