After a successful winter indoor campaign, which saw the Club claim three trophies, the 2019 season got underway on Easter Sunday when the Friendly XI visited Putney CC for the first time. Dave Brown's side were the success story of the first half of the season, and they started with a seven wicket win. Nicky Ison, Will Frost and Will Bottoms picked up two wickets apiece, but it was the captain who stole the show with the ball as his 3-18 helped to restrict Putney to 196-9. Frost and Stewart Hammond got the reply off to a good start before an unbeaten half century from Ison and runs from Ollie White saw Upminster to victory. The next day, Easter Monday, saw the 1st XI in action for the first time, as they entertained a Wanstead & Snaresbrook XI. Alan Ison (88) and Louis Pickering (77) helped the home side to 239-4, before two wickets for each of Ollie Peck, John Curtis, Sam Twine and Shahbaz Butt saw Wanstead bowled out for 92.
Unfortunately the first competitive senior action of the season saw defeat as the 1st XI crashed out of the League Cup on the final Saturday of April. Louis Pickering bowled well and picked up three wickets, and there was a brace of wickets for Nicky Ison and Shafiq Rahman, but Wood were still able to pile up 276-8 from their 50 overs, with captain Craig Perrin making a half century. In reply Shahbaz Butt and Kiran Kullar got Upminster off to a good start, but when they fell things quickly went downhill and Upminster were bowled out for 148. Wood also came out on top in the friendly match between the two club's 2nd XIs back at Upminster Park. Upminster's batsmen struggled to get going but youngsters Will Frost, Max Gordon and Nathan Bright helped them to make it to 125-7 from their 40 overs. It was never enough though and Wood won by seven wickets.
The following day the 1st XI reached the second round of the National Cup after Kent side Roebucks conceded, while there was another win for the Friendly XI in a thrilling game at Holtwhites-Trinibis. Paul Middlemiss made 66 and Oliver White and Kevin Roome were also in the runs as Dave Brown's side made 191-9 from their 40 overs. 79 from Gareth Garnsworthy looked to be taking Holtwhites to victory but wickets fell late on and Mark Schofield held his nerve when bowling the last over as Upminster squeezed home by one run.