The Gills are on the cusp of the playoff race and experiencing a resurgence under Steve Lovell. The playoffs are a secondary goal for teams who have found themselves marooned in mid-table without hope of catching the leaders.
As Gills fans know, the end-of-season lottery is not always kind. Many still shudder at the words ‘Manchester City’. The current superpowers were just minutes from being beaten in the 1999 final, but fate played a hand and the Gills were left to suffer another season in the third tier.
You have to cast your mind back a little further though to understand the apprehension with which some Gillingham fans view the playoff finals. Back in 1986/87, they were brand new, an experiment of sorts that ended up becoming part of our football heritage. Fans of a certain age will remember all-too-well the misfortune that befell our blue-shirted heroes that season, but for anyone under the age of 30, prepare for a brief history lesson.
Thirty years ago, it was only the top five teams in the promotion hunt; two went up automatically and the next three were involved in the playoffs. The fourth side making up the semifinals were from the division above, in this case, Sunderland. Having finished fifth, the Gills had to play their higher-ranked opposition, whilst Swindon met Wigan in the other semifinal.
Sunderland came to Priestfield on May 14th, 1987 for the first time in their history and despite an early goal, they lost the tie 3-2 thanks to Tony Cascarino’s second-half hat-trick. That gave the Gills a golden opportunity to advance to the two-legged final.
Sunderland had two away goals, though, and that meant a solitary goal for them would send them through to the final. The 25,470 crowd were soon silenced in the second leg as Gillingham extended the lead. Sunderland fought back bravely, scoring twice to lead on away goals.
Sunderland keeper Ian Hesford then saved a Colin Greenall penalty, but the resulting scramble gave Cascarino his fourth of the tie. With just two minutes of normal time remaining, Gary Bennett nodded in a third for Sunderland, sending the tie into extra time as even away goals couldn’t separate the sides. Within two minutes of the restart, Cascarino scored for Gillingham. 3-3 on the day, 5-4 on aggregate but crucially leaving Sunderland needing two goals to win the tie. Keith Bertschin scored one, Sunderland were relegated and Gillingham went on to face Swindon in the final.
Gillingham, who are currently 40/1 to finish in the current League One playoffs in the football betting, were the underdogs in 1987. Swindon had finished nine points clear in third and felt promotion was rightfully theirs.
The Gills won their home leg, against the run of play, 1-0. Swindon had been by far the better side and quickly took a 2-0 lead in the second leg. However, another late Gills goals saw them bring the tie to 2-2 on aggregate. Cruelly, the final had no away goals rule which meant a third game.
After 46 matches, the Gills faced their fifth match in 15 days and this time, there was no reprieve. Swindon won 2-0 and were promoted to Division Two, and the Gills were left ruing their luck. A rule change in 1990 meant the final was played at Wembley Stadium, but the Gills will remain in history with the dubious honour of being the side eliminated in the first Division Three playoff final.