The O’s got off to the perfect start when Massey slotted home at the back post with just three minutes on the clock, however, after a spell of pressure in the second half substitute Waters’ deflected strike saw both sides pick up a point.
O’s boss Andy Hessenthaler handed debuts to new signings Tom Parkes, Yvan Erichot, Harry Cornick, Robbie Weir, Gavin Massey and Jordan Bowery, while Jay Simpson missed out.
Orient started the last campaign with a 2-0 victory over then National League champions Barnet, and they got off to the perfect start at Whaddon Road, scoring the fastest goals of the 3pm kick-offs in the Football League season.
Just three minutes were on the clock when Sandro Semedo produced a fine curling ball from the left into the back post and summer signing Gavin Massey was left with the simplest of finishes to slot the ball past Russell Griffiths in the Robins goal.
Semedo continued his fine start down the left, getting forward as much as possible and he once more found goalscorer Massey with a delivery, however this time the former Colchester man fired his shot over the bar.
The O’s had started promisingly and loan signing Cornick did well to dispose the hosts of the ball before playing in Jordan Bowery and his effort was held by Griffiths at full stretch.
One should have been two on 17 minutes though as a corner routine caught the hosts offguard with Robbie Weir playing it to an unmarked Semedo on the edge of the box but he shot was just off target.
Chances were few and far between for the hosts in the opening exchanges, and the closest they came to testing Alex Cisak in the Orient goal saw Danny Whitehead come forward from midfield and tried his luck from 25 yards out, however, the strike was easily for Cisak to hold.
They began to work their way into the game though and on the half hour mark it was only a fine block from Sean Clohessy who denied Amari Morgan-Smith a shot on goal, before appeals were waved away for a penalty when Semedo and Morgan-Smith tangled in the box.
Cornick produced a bit of magic for the O’s down the left as he managed to weave his way away from two home defenders before coming inside on to his right and firing low across goal, only to see the ball blocked.
The game began to open up even more and up the other end a ball in from James Rowe found the head of Dan Holman, but the striker was always reaching for the effort and the attempt was off target.
Neither side made changes at the break as Orient looked to build on their one-goal advantage and the first opportunity of the second period went to the hosts as a Daniel O’Shaughnessy long-throw was flicked towards his own goal by Parkes.
Shortly after Massey went on to force a good save from Griffiths in the Robins goal, as he parried his 20-yard effort behind for another O’s corner.
The game was certainly becoming end-to-end and there were a few nervy moments for the O’s defence but they were putting their bodies on the lines and blocks were coming in from all angles.
Orient still looked dangerous on the attack though and a quick breakaway from Cornick found Bowery with plenty of space to run into. He took one touch before unfortunately losing his balance and shooting wide.
A free-kick was won in a dangerous position moments later and Cornick forced Griffiths into a fine save low down to his left.
Not for the first time O’Shaughnessy’s long throws were causing Orient problems, and another one presented Dan Holman with an opportunity from close range, however the striker squandered the chance.
Moments later Cisak came out well to gather under pressure, before Danny Wright spurned another opportunity when the ball fell to him just on the edge of the box, but scuffed his effort and Cisak was able to hold.
At times the O’s goal was living a charmed live, and Cisak was called into action once more, this time to deny O’Shaughnessy’s header, before the rebound was fired over.
It didn’t survive for much longer unfortunately as the hosts forced an equaliser with 14 minutes remaining as Whitehead’s ball across was met by substitute Billy Waters and his shot, with an aid of deflection, found its way into the bottom corner.
Orient remained undeterred by the levelled and with 10 minutes to go a good run from Massey found Palmer in the box and after taking a touch his shot was blocked and the hosts cleared the danger.
Five minutes of stoppage time were awarded, and though both sides tried to force a late winner neither could find a way and the opening day encounter ended all square.
Cheltenham Town: Griffiths, Jennings (Cranston 65) , Parslow (c), O’Shaughnessy, Suliman (Barthram 65), Rowe (Waters 71), Whitehead, Pell, Morgan-Smith, Wright, Holman.
Subs: Kitscha, Lynn, Bower, Thomas.
Goals: Waters (76)
Bookings: Suliman (36)
Orient: Cisak, Semedo, Parkes (Hunt 77), Erichot, Clohessy, Cornick, Atangana, Weir (c) (Kelly 71) , Massey, Bowery (Gnanduillet 81), Palmer.
Subs: Sargeant, Kennedy, Cox, Koroma.
Goals: Massey (3),
Bookings: Atangana (55), Cornick (90).
Attendance: 3,912 (815 Leyton Orient supporters)