1901
From the outset, the Club ran two sides with "Buddy" holding the post of 1st XI Captain. The first game the 'new' Upton Cricket Club 1st XI played was on 18th May 1901 against EH Biglands XI. A victory was gained in a low scoring game, with Upton being 61 all out, the opposition being 31 all out. Unfortunately, limited playing records exist for the first season, however one noticeable point is the number of low scoring games. On 24th September, the 1st XI were dismissed for a total of 4 runs by Sefton 3rd XI at Upton. These low scores are normally attributed to the fact that a new square was in use, but it is strange to relate that a report in the Birkenhead News praised A Calvert for the preparation of an excellent wicket.

The only notable batting performance in the inaugural season was a score of 54 by LW Court against West Derby 2nd XI at Upton. There was however several outstanding bowling performances, CS Hannay (brother of "Buddy") taking 6 wickets against Wavertree at Upton, 5 wickets away to Great Saughall, and 8 for 18 against Oxton 3rd XI at Oxton. C Lewis taking 5 for 29 against West Derby 2nd XI at Upton, T Phillips taking 6 wickets away at Prenton, J Harris taking 5 wickets against Cable Companies, and G Alcock taking 9 for 33 against LiverpoolCaledonians at Upton, and 5 wickets away to Old Xaverians.

The 1st XI were represented in its inaugural season by:

In the first season, matches were played against:

Meagre records exist for the 2nd XI, where again low scores were the fashion, and in four matches recorded, two were won and two were lost. G Alcock and D Fraser each took 5 wickets at home to Prenton 2nd XI, whilst E Goodwin took 5 wickets at home to Hoylake.

In a very low scoring match on 15th June 1901, Hoylake were dismissed for 32 runs, whilst Upton could only muster 26. On 27th July, Hoylake were dismissed for only 46 runs at Upton, and on 31st August, Trinity Wesleyans were dismissed for only 17 runs and only 25 runs in their second innings, Upton winning by an innings and 13 runs.

The 2nd XI were represented in its inaugural season by:

1902
The 1902 season was much better for the 1st XI, playing a recorded number of 22 matches, winning 9, losing 8, 2 were drawn, 1 was rained off and no results being available for 2 of the fixtures.

Outstanding performances included; A Calvert scoring 219 runs, "Buddy" scoring 161 runs, CS Hannay scoring 157 runs including 104 against Sefton AN XI at Upton (the first in the Clubs history) and 53 at home to Northern 3rd XI, and B Hancock scoring 63 at home against Sefton 3rd XI.

On the bowling scene G Alcock took 53 wickets including the outstanding feat of 10 for 20 against Old Xaverians at Upton including a hat-trick (the first for both feats in the clubs history), 5 for 19 away to Liverpool Caledonian, 6 for 9 away at Oxton 3rd XI, 7 wickets at home to Birkenhead Park 2nd XI and 6 wickets away at PSNC. A Calvert took 51 wickets including 5 wickets at home to Wallasey 2nd XI, 6 for 34 at home to Wavertree 3rd XI and 6 for 15 at home to Northern 3rd XI. In addition, LW Court took 6 for 28 (1st innings) and 7 for 9 (2nd innings) at home to Sefton 3rd XI, Upton winning by an innings and 71 runs, and CS Hannay taking 6 for 30 at home to Sefton AN XI. In the field, JW Sandbach took 11 catches.

The highest score recorded by Upton during the season was 190 for 5 at home to Sefton AN XI. Lowest scores included Liverpool Caledonian 49 all out (G Alcock taking 5 for 19), whilst in replay Upton could only achieve 38 all out. Following the low scoring trend of the previous season, there were several other games where neither side could score over 50 runs.

Once again, little information is available for the 2nd XI, and out of the six matches recorded, four were lost, with two being cancelled due to Upton being unable to raise a team.

The only outstanding performances were with the ball with J Harris taking 5 for 43 at home to Liverpool Caledonians 2nd XI, and H McLelland taking 7 wickets at home to Tranmere Wesley 2nd XI.

Low scores also figured prominently for the 2nd XI; 26 all out at home to Liverpool Caledonians, 34 all out at home to Tranmere Wesley, 30 all out away at Great Saughall, and 33 all out at home to Liscard.

1903
Of the 21 recorded fixtures for the 1st XI, 4 were won, 1 was tied, 5 were lost, 1 was drawn, 2 games were rained off, with no information being available for the remaining 9 games.

A Calvert was proving his worth as ‘Club professional’ as he scored 67 not out against Wallasey 2nd XI, ‘Buddy’ played a captains role in scoring 53 against West Derby 2nd XI at Upton, ably supported by LW Court scoring 58 in the same match, and also 89 against Wallasey 2nd XI.

On the bowling scene, there were several outstanding performances from A Calvert taking 5 for 33 against Cable Companies at Upton, 7 for 22 against West Derby 2nd XI at Upton including a hat-trick, 5 wickets against Old Xaverians away, 8 for 42 against West Derby 2nd XI away, and 5 wickets for CS Hannay’s XI against C McKinnear’s XI at Upton. C Lewis took 5 for 41 against Cable Companies at Upton, 5 wickets against Sefton 3rd XI at Upton, 5 wickets against Cable Companies at Upton, and ‘Buddy’ chipped in with 5 wickets against Cable Companies at Upton.

Highest scores by Upton were 189 all out against Wst Derby 2nd XI at Upton, and 222 for 5 declared against Wallasey 2nd XI. These two high scores wereoffset by notably low scores off 44 all out against Old Xaverians and 29 all out against West Derby 2nd XI.

1904
Season 1904 saw the Club gain a new member in DQ Steel. He would go on to serve the club with distinction both on and off the field for many years, being Chairman from 1913 to 1926, and he would go on to score 4,950 1st XI runs, of which 817 were scored in his debut season.

A Calvert was the main bowler, taking 94 wickets during the season, including a 9 wicket haul against Neston. Quite remarkably he surpassed this when he took all 10 wickets for only 11 runs against Oxton.

1905
Although no information is available regarding the adminstration of the Club, the year 1905 must have seen the Club making tremendous progress as plans must have been put in hand for a new pavilion.

The 1st XI had a successful season, wirth the batting dominated by 'Buddy' (623 runs), and DQ Steel (591 runs). The bowling was again dominated by A Clavert who took 57 wickets, DQ Steel chipped in with 38 wickets and H McClelland took 37 wickets.

1906
The year saw a number of changes, for not only was the new pavilion constructed, but there was a number of changes in the playing structure.

Despite heavy rain for the first few weeks of the season, the 1st XI had a very sucessful season. The batting was dominated by DQ Steel (628 runs), 'Buddy' (423 runs), and A Calvert (377 runs). To add to their fine run total, A Calvert took 65 wickets, and 'Buddy' took 49 wickets.

1907
The club was strengthened by the arrival of two new members; LC Ord and J Hooton. The latter would go on to form a very formidable bowling partnership with A Calvert.

Unusually, the 1st XI had a mediocre season in comparison to previous years. There were polite comments made in the press regarding the fact that the bulk of the Club's fixtures were played at home, with any away games that were arranged being against local sides. The exception being the fixture against Eaton Park in the estate of the Duke of Westminster.

DQ Steel was again the leading run scorer with 645 runs, ably supported by 'Buddy' (392 runs) and in his debut season, LC Ord (325 runs).

A Calvert again topped the bowling charts with 55 wickets, supported by J Hooton (37 wickets) and 'Buddy' contributing 29 wickets

1908
There were still mumblings in the press concerning the fixtures that the Club were playing, however the Club broadened their horizons with new fixtures.

With the dominance of recent years by key individuals, it was pleasing to note that promising all-rounder, W Owens, led the way with the bat scoring 389 runs, including 101 not out against Anfield. 'Buddy' weighed in with 383 runs and LC Ord with 307. It was an unusually quiet season for DQ Steel, as he only scored 256 runs.

On the bowling scene, A Calvert led the way with 41 wickets, ably supported by J Hooton with 31 wickets. 'Buddy' continued his fine all round form, taking 25 wickets.

1909
It was now becoming apparent that the Club was producing some very useful all-round cricketers. During a successful season for the 1st XI, A Calvert was prominent. He scored 480 runs and took 67 wickets. The captain, 'Buddy' scored 479 runs, took 24 wickets and held 14 catches. J Hooton also took 67 wickets, including two eight wcket hauls, with both W Owens and J Harris scoring over 400 runs.

A notable figure to emerge during the season was WN Derryman, who was over a period of two decades, set to dominate the wicket keeper's berth, and whilst not a very good bat, was possibly the best wicket keeper the Club has ever had. In his 286 1st XI games, he made 206 stumpngs and took 174 catches, a record that will be hard to beat.

1910
From a playing point of view, season 1910, the Club’s tenth anniversary, was a mediocre one, winning only five of their eighteen games. The free scoring of certain batsmen was not so prominent during the season, with W Owens leading the way with only 276 runs. J Hooton was the lading wicket taker with 70 wickets, including seven wickets on two occasions.

The fixture against the Cotton Exchange at Upton over two days, differed from a normal fixture in that the visitors utilised thirteen players, whilst Upton called on twelve, and the visitors who only scored 83 in their first innings, scored 256 for 9 in their second innings in replay to Upton’s 201 for 8 declared.

The first ten years of the Club’s existence had proved quite satisfactory, having made a predictably slow start into the arena of organised local cricket, the club had established itself and strengthened both its player base and fixture list, with fixtures as far away as Buckley and Chester, although a number of guest players had been introduced from time to time to deliberately strengthen the side for strong fixtures.

The Club was about to enter a halcyon period, which lasted up to the start of the First World War, and fortunately, complete records for the 1st XI for the period 1911 to 1933 inclusive, written in beautiful copper plate writing, and contained in three leather bound volumes have survived and were rescued by DI Jones from the old pavilion before it was demolished in 1972.

Whilst most of the established “old guard” were once again on parade, several significant changes took place. The name of W Owens, who had performed admirably as an all-rounder for a couple of seasons, was missing, and apart from WN Derryman who had already begun to emerge as a great prospect, another new name appeared; A Wildgoose, an all-round cricketer who’s performances over the next twenty year period, established him as possibly the greatest all round cricketer the Club has been fortunate to possess.