The 1st season of the 20th Century saw East Stirlingshire FC in the Scottish League for the 1st time after our successful application. In 1900/01 the club were not only playing in the Scottish Division Two but also continued to play in the Falkirk & District League with both sets of League games being played throughout the season. The season opened with a convincing 8-2 home win in the local league against Falkirk Amateurs but the main event for everyone involved with the club and the fans was the 1st ever Scottish League game on 18th August at Merchiston Park against Airdrieonians. A crowd of 2500 turned up to watch the Shire lose narrowly, 2-3 (Shire had also missed a 2nd half penalty). Shire’s team in that 1st Scottish League game was:                                                                                                   William Allan, Peter Hunter, Jimmy Johnston, Andrew Prentice, Wull Morris, Peter Steele, John Dobbie, Thomas Laidlaw, James Shearer, David Gillespie, John Reid. Wull Morris having the honour of been the scorer of Shire’s 1st ever Scottish League goal.                                                                                                                                                   Shire did win our 1st ever Scottish League game away to Motherwell 3-0 the following Saturday, which turned out to be only 1 of only 2 away wins in the League that season. Home form was better and included a 5-2 triumph over Hamilton Academical in May 1901. Shire ended up 7th in the 10 team League and the crowds for every home game had been 1500 or more. In the Falkirk & District League Shire didn’t complete our fixtures and ended 5th out of 6th. During 1900/01 we had a run all the way again to the Scottish Qualifying Cup Final beating, Raith Rovers, Bo’ness and Orion amongst others in earlier rounds. Over 6000 fans turned up on 15th December to watch the Final against local rivals, Stenhousemuir. Unfortunately it wasn’t to be Shire’s day losing 0-3. In the Scottish Cup 1st Round we lost heavily 0-6 away to Clyde. Shire also reached the Final of the Dewar Shield but lost 1-6 at Dens Park to Dundee. It was reported that the match was filmed by 2 cameras, the 1st ever Shire game to have been filmed. E.S. regained the Stirlingshire Cup beating Camelon 3-2 in the March Final. At the end of the season Shire played in the Falkirk Cottage Hospital Shield but went out 0-1 against Falkirk at Bainsford in the Semi-Final replay.  In December there was a 1st report that the club may have to move from Merchiston Park in the future due to a railway line being built where the ground stood and this was confirmed in April that the club would indeed lose our ground.

The following season was not a great one for the club. In an expanded Scottish Division Two of 12 teams Shire were placed 9th, although we did win 8 games. It took until our 7th league game of the season to record our 1st win when a good 4-1 result was achieved at Merchiston Park against Hamilton Academical. It wasn’t until the end of the campaign that our form finally clicked, winning 4 or our last 6 games against Leith Athletic, Clyde, Motherwell and Ayr (the last three away from home). For the 1st time since 1896/97 Shire didn’t qualify for the Scottish Cup disastrously going out in the 1st Round of the Scottish Qualifying Cup 1-2 away to Falkirk in front of a 5000 crowd on 7th September. The Stirlingshire Cup was only slightly better losing out away to Stenhousemuir in the Semi Final in February. Due to going out in the main competition Shire got a 2nd chance of glory in the Stirlingshire Consolation Cup (for teams knocked out in the earlier rounds of the Stirlingshire Cup) but again we came up against Falkirk in the Semi Final at Brockville Park and went out 0-2. Shire did get to the Final of Falkirk Cottage Hospital Shield at the end of May but lost at home 0-1 to Falkirk. As consequence of going out earlier in the Cups Shire played a number of friendlies that season including games against Celtic, Falkirk and Stenhousemuir. One positive from the season is that crowds at Merchiston Park remained good with attendances usually between 2000 to 3000 for the League matches.

The next season 1902/03 local rivals, Falkirk joined the Shire in Scottish Division Two and suddenly local Derbies were being competed on the highest stage. Shire would continue to struggle to make our mark in the League ended up 8th in the 12 team League though the campaign had gotten off to a better start with 4-1 wins against in the 1st two games against Raith Rovers and Leith Athletic. The 1st ever Scottish League Falkirk derby took place in the next match on 30th August when a crowd of 4000 at Merchiston Park witnessed the Brockville Park team win 2 nil. For the 2nd season in a row Falkirk defeated the Shire in the 1st Round of the Scottish Qualifying Cup 0-1 in front of a 5000 crowd at Merchiston Park. There were better news in the Stirlingshire Cup when we were triumphant in April 3-0 against Stenhousemuir in a Replayed Final at Brockville Park. Following on from this Shire played a Semi Final match in the Dewar Shield against Victoria United in Aberdeen but lost 0-2. The Falkirk Cottage Hospital Shield was a League for 1902/03 but Shire failed to beat Falkirk, Camelon and Stenhousemuir in any of the matches and ended up last. There was a one off tournament at the start of the season called the Ibrox Disaster Fund- Stirlingshire Coronation Competition which Shire won after beating Stenhousemuir 1-0 in a Replayed Final. After the Ibrox Disaster Shire had pulled down our grandstand at the start of the season due to being condemned due to safety regulations. There was report towards the end of the season in the Falkirk Herald regarding a possible merger of East Stirlingshire and Falkirk to form a Scottish Division One team. At the AGM at the end of the season the club announced that as the stay at Merchiston Park would be for at least 2 years a new stand would be built during the close season though this appears never to have been built.

At the start of 1903/04 Shire played a testimonial match against Dundee at Merchiston Park for two true E.S. clubs legends, Davie Alexander and Peter Steele. This was the 1st ever testimonial the club has played for any of our players and both players deserved the honour. Davie is to this day still the club’s record overall record known goalscorer and Peter was at the time the club’s all-time record appearance maker (though 2 players have now surpassed his total). The League campaign proved to be a far better one that season for the Shire as we ended up 6th in the 12 team Scottish Division Two (our best season so far in the national league). Highlights for the League games included a 3-0 home win against Raith Rovers and a 1st ever Scottish League win against Falkirk on 9th January when a 2-1 result was achieved at Merchiston Park.  Unfortunately Shire failed for the 3rd season in a row to reach the Scottish Cup going out in the 3rd Round 3 nil away to Alloa Athletic after wins against Camelon and Stenhousemuir in the earlier rounds. The Stirlingshire Cup Final was reached for the 2nd year in a row but Falkirk edged us out 3-4 to lift the Cup. The Falkirk Cottage Hospital Shield was again a Cup competition and Shire won it in May thanks to a 4-1 Final win against Falkirk. Shire also competed in a one off end of season Cup called the Central Counties Championship and after a 6-0 Semi Final against St. Johnstone we lost the Final 0-5 to Raith Rovers at Starks Park. During the season the club learned that their tenure at Merchiston Park was actually going to end as a branch railway line, to the local iron works, was planned to be built directly through were the ground stood was confirmed. The search for a new ground was on. In May both East Stirlingshire and Falkirk applied to join the Scottish Division One but were declined.

The next season Shire only achieved 9th place in Division Two winning 7 of our 22 games. Home form remained competitive and included wins against Falkirk (2-0), St, Bernard’s (4-0) and Albion Rovers (5-2) but away performances were very poor with only 1 win achieved against Leith Athletic in the penultimate away match. It was the same recent story in the Scottish Qualifying Cup losing in the 3rd Round and therefore failing to reach the Scottish Cup Proper. This time it was Non-League Cowdenbeath who knocked Shire out 1-2 at North End Park in a replay. Shire did reach the Stirlingshire Cup Final but lost 0-1 to Alloa Athletic at Brockville Park in front of a 4000 crowd. The Cottage Hospital Shield was re-named the Falkirk Infirmary Shield and Shire met Falkirk in the Final that season losing 1-3. Shire also played a lot of friendlies that season including a home match against Sunderland in May. Sunderland had just finished 5th in the English Division One (the top league at the time) and Shire did well to lose narrowly 1-2. One of the pivotal events in East Stirlingshire’s history took place in March.  On the 11th March East Stirlingshire and Falkirk held Special General Meetings to discuss the proposed amalgamation of the clubs with a view to forming a Division One club. In a 1 hour meeting Falkirk agreed to the amalgamation. However, in a much longer meeting the Shire decided against it on the casting vote of the Chairman. Whilst E.S. stalled Falkirk two weeks later pressed on and formed a Limited Company and subsequently applied to join the Scottish Division One and were successful. Shire did hold a meeting in May to form a Limited Company but the decision was deferred for 6 months. For East Stirlingshire the moment in history had gone.

1905/06 was a terrible season on the playing front for the club. The failed merger with Falkirk from the previous season and Falkirk promotion changed the balance of footballing power in the town in favour of the Dark Blues and apart from the gradual transferring of fan allegiances over the coming seasons to the Brockville side the quality of players that Shire were able to attract from the local player pool was hit hard. Only 1 League game was won that season, away to Ayr 4-1 in November, and it is unsurprising that Shire ended up bottom of the 12 team League. Being the bottom club Shire had to stand for re-election to the League which we were successful in. The now annual defeat in the 3rd Round of Scottish Qualifying Cup happened in September, this time a 1-2 away defeat at Leith Athletic. Even in the local Cups Shire failed to make our mark losing in the Stirlingshire Cup Semi Final to Alloa Athletic, the Stirlingshire Consolation Cup 1st Round at home to King’s Park and in the Falkirk Infirmary Shield the Semi Final 1-2 against Stenhousemuir. E.S. also played in the 1st ever Penman Cup going out to Cowdenbeath in the 3rd Round, a 1st game had been drawn 3-3 and it is unknown if a replay was played or if Shire withdrew. The Penman Cup was a competition for teams from Fife, Clackmannan, Edinburgh, Linlithgowshire and Stirlingshire. In December it was confirmed that the Club would be leaving Merchiston Park at the end of May. By April it had decided that the new ground would be located only a very short distance away where the club had 1st played football in 1880/81 and again from March/April 1882 to April 1883.

Shire worked hard over the close season moving the short distance to the new ground which was formally opened on the 1st day of the season, 16th August 1906, against Clyde. The ground was named New Merchiston Park to differentiate from the old ground though it wasn’t too long before it was just called Merchiston Park. William McNair put the Zebras (as we were known at the time) 1 nil up at the break but Clyde tied the game 1-1 before full time. Whilst still struggling on the pitch Shire did end up only 2nd bottom in 11th place in the League in season 1906/07. That 11th place had been decided by a play-off match against Raith Rovers who had ended up on the same points. Raith won the match 3-2 consigning Shire to stand for re-election with bottom team Ayr Parkhouse. However, both teams were successfully re-elected at the Scottish League AGM on 27th May. Like the previous few seasons Shire went out earlier in the Scottish Qualifying Cup losing 1-0 to fellow Division Two team, Arthurlie, 0-1. Shire had mixed success in the other Cups, wining the Stirlingshire Cup with a Final win against Alloa Athletic 2-0 in front of a very large 5000 crowd, though they went out to Falkirk in the 1st Round of the Falkirk Infirmary Shield 1-2 and to Aberdeen A in the Dewar Cup Semi Final 2-0 at Brockville Park.

There was a marked improvement in the 1907/08 Shire team. The Division Two re-election scares of the previous 2 seasons were a distant memory as the Zebras achieved our best League placing to that time of 5th. In fact, a poor start had cost us a higher place, it took to our 5th game to win our 1st game. The home form was particularly impressive losing only 2 games, the 1st home game of the season to Arthurlie and the last to the champions, Raith Rovers. Despite again missing out on the Scottish Cup Shire were only knocked out of the Scottish Cup Qualifying Cup at the 3rd Round in a replay away to Raith Rovers. A new Scottish Consolation Cup was introduced that season for teams who had played in the Scottish Qualifying Cup but failed to the reach the Scottish Cup and Shire managed to reach the 4th Round before losing out to fellow Division Two side, Leith Athletic. Shire also reached the Final of the Stirlingshire Cup but it was Alloa Athletic who won the replayed Final 1 nil. We also played in the Penman Cup reaching the 3rd Round winning 1-0 against Alloa Athletic but the competition wasn’t completed that season. Of interest is, with a free date on 1st January Shire travelled to Inverness Caledonian for a friendly and it wasn’t a surprise that we lost 1-3 given we had played a Penman Cup game only 24 hours before. In January Walter Clarkson, one of the most important Club Officials in our history, was elected Club Secretary.

Whilst not setting the heather on fire in the League in 1908/09 there were a few league highlights including two draws against the eventual champions, Abercorn, and a win and draw and 3rd placed Vale of Leven. Shire were tied for 7th place at the end of the season and placed 9th on goal average. The Scottish Qualifying Cup proved to be successful with Shire reaching the Quarter Final where we met Leith Athletic on 31st October in front of a 5000 crowd (which included 2 special trains run for E.S. fans) at Old Logie Green in Edinburgh. Although Shire lost 0-2 we had reached the Scottish Cup for the 1st time since 1900/01. As fate would have it we were drawn away to Falkirk in the 1st Round and a huge crowd of 7000 saw the Shire go down narrowly 1-2 to the Division One team (Falkirk would reach the Semi Final of the Scottish Cup that season). During the season we played in two Penman Cup competitions, the 1st was the uncompleted 1907/08 Cup which Shire gained the Runners Up place after losing in the Final 0-1 to St. Bernard’s at Brockville Park. In the 1908/09 version we reached the Semi Final before succumbing to Raith Rovers 0-3 in Kirkcaldy. Shire didn’t progress beyond the Semi Finals in either of the Local Cups, losing to Falkirk in a Replay in the Stirlingshire Cup and King’s Park in the Stirlingshire Consolation Cup. One statistical quirk from the season was for the 1st time since the club was formed in 1880 no friendly matches were played during the season though a benefit match took place against Celtic to raise funds for former Shire captain John Reid who was seriously ill. In September the club had long standing President of over 20 years, ex-Baillie James Young died. He had been the clubs 1st ever patron and the club had rented fields on his farm for our various grounds. It was reported that in February Junior football games were still being played at the original Merchiston Park and that that fans watching games there would stay and the watch the Shire game at New Merchiston Park from the “mound”.

The last season of the decade saw the club continued to perform as a solid Division Two side. Season ticket sales were up, treble that of the previous season. Although the Shire would end up in 8th place in the League we were only 3 points off 4th place.  Shire we unable to reach the Scottish Cup as we had done in the previous season going out in the 2nd Round of the Scottish Qualifying Cup away to Bathgate (500 Shire fans had travelled to the game by special train). As result E.S. entered the Scottish Consolation Cup and got through to the Quarter Final of the competition before losing 0-2 at Sanquhar against Nithsdale Wanderers. In the minor Cups Shire met Falkirk in the held over 1908/09 Falkirk Infirmary Shield Final with the Division One side winning 4 goals to nil. Shire did reach the 3rd Round of the Penman Cup and were drawn to play East Fife. It is unknown if the game was ever played or if Shire withdrew, what is known is that East Fife were the team who went through to the next round. In March Shire met Falkirk again this time in the Stirlingshire Cup Semi Final. A record crowd at that time for New Merchiston Park of 3000 saw Shire lose out 1-2. In November the club formed a committee to look at forming a Limited Company and the club finally agreed to the change 2 months later. The club official became East Stirlingshire Football and Athletic Club in June. Despite Shire having to move out of the old ground at the end of season 1909/10 Juvenile games continue to be played there throughout the season.